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Water → 4-[(4,5-Difluoro-2-methoxyphenoxy)methyl]-N-(triphenylmethyl)-1-piperidineethanamine

HRID 248347
Notes
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Reaction equation

HRID 248347 reaction equation
Cl.[F:2][C:3]1[C:16]([F:17])=[CH:15][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[C:5]([O:18][CH3:19])[CH:4]=1.Br[CH2:21][CH2:22][NH:23][C:24]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:2][C:3]1[C:16]([F:17])=[CH:15][C:6]([O:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:21][CH2:22][NH:23][C:24]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:11][CH2:10]2)=[C:5]([O:18][CH3:19])[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15718287(2-Bromoethyl)tritylamineHCID 197633674-[(4,5-Difluoro-2-methoxyphenoxy)methyl]piperidine hydrochloride

Product 1

HCID 197633854-[(4,5-Difluoro-2-methoxyphenoxy)methyl]-N-(triphenylmethyl)-1-piperidineethanamineYield 41.5%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

5.88 g (0.020 mol) of 4-[(4,5-difluoro-2-methoxyphenoxy)methyl]piperidine hydrochloride, 7.7 g (0.021 mol) of 2-bromo-N-(triphenylmethyl)ethylamine and 6.91 g (0.050 mol) of K2CO3 in 40 ml of DMF are reacted. The reaction mixture is heated to 90° C. for 8 hours. It is cooled to room temperature, poured into 500 ml of water and extracted 3 times with ethyl acetate. The organic phases are combined, washed with water, dried over MgSO4 and filtered, and the solvent is evaporated off under reduced pressure. The product is obtained in the form of an oil after chromatography. Yield: 41.5%.

Workup

  1. temperatureIt is cooled to room temperature
  2. extractionextracted 3 times with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is evaporated off under reduced pressure
  7. customThe product is obtained in the form of an oil after chromatography

Sources & evidence

ORD record
ord-d32e64f01da745f7a4d7dbc8a579c938
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05210086

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes