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Sodium Bicarbonate → Acetamide,N-[2-[3,4-dihydro-7-[[[(3R,4R)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]-3-piperidinyl]oxy]methyl]-1(2H)-quinolinyl]ethyl]-

HRID 1531481
Notes
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Reaction equation

HRID 1531481 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])=[CH:16][CH:15]=2)[C@@H:10]([O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][CH2:47][NH:48][C:49](=[O:51])[CH3:50])=[CH:38][CH:37]=2)[CH2:9]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCCl.[Br-].[Zn+2].[Br-]>[CH3:33][O:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:24][CH2:23][CH2:22][CH2:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C@H:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]2[O:34][CH2:35][C:36]2[CH:45]=[C:44]3[C:39]([CH2:40][CH2:41][CH2:42][N:43]3[CH2:46][CH2:47][NH:48][C:49](=[O:51])[CH3:50])=[CH:38][CH:37]=2)=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 11262561(3R,4R)-3-[1-(2-acetylamino-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 9851682Acetamide,N-[2-[3,4-dihydro-7-[[[(3R,4R)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]-3-piperidinyl]oxy]methyl]-1(2H)-quinolinyl]ethyl]-Yield 48%

Reagents, catalysts & solvents 2

HCID 10421208
Zinc bromide
Catalyst
HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 0.88 g (1.25 mmol) of (3R,4R)-3-[1-(2-acetylamino-ethyl)-1,2,3,4-tetrahydro-quinolin-7-ylmethoxy]-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidine-1-carboxylic acid tert-butyl ester in 9 ml of 1,2-dichloroethane was treated with 0.62 g (2.75 mmol, 2.2 equiv.) of anhydrous zinc bromide. The suspension was stirred for 2 h at 50° C. under Argon atmosphere. Subsequently, it was poured into a mixture of 100 ml of ice/water and 10 ml of sat. sodium bicarbonate solution. The aqueous phase was extracted five times with 50 ml of ethyl acetate. The combined organic phases were washed three times with 20 ml of water, dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The thus-obtained crude product was purified by chromatography on silica gel using a 100:10:1 v/v/v mixture of dichloromethane/methanol/28% ammonium hydroxide solution as the eluent and yielded 0.36 g (0.60 mmol, 48.0% of theory) of (3R,4R)-N-[2-[7-[4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-3,4-dihydro-2H-quinolin-1-yl]-ethyl]-acetamide as a light yellow oil; MS: 602 (M+H)+.

Workup

  1. extractionThe aqueous phase was extracted five times with 50 ml of ethyl acetate
  2. washThe combined organic phases were washed three times with 20 ml of water
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customdried in a high vacuum
  6. customThe thus-obtained crude product
  7. customwas purified by chromatography on silica gel using
  8. additiona 100:10:1 v/v/v mixture of dichloromethane/methanol/28% ammonium hydroxide solution as the eluent

Sources & evidence

ORD record
ord-75a1ef8af52449768aa63d478b2e85e2
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06197959B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes