Hydrochloric Acid → 4-Benzyl-6-[2-[4-(ethoxycarbonylamino)-4-phenylpiperid-1-yl]ethyl]-6-(3,4-dichlorophenyl)morpholin-3-one hydrochloride monohydrate

HRID 849347Notes

Reaction equation

HRID 849347 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)([CH2:14][CH2:15]OS(C)(=O)=O)[O:11][CH2:10][C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[CH2:37]([O:39][C:40]([NH:42][C:43]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)=[O:41])[CH3:38].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.C(Cl)Cl.CCOCC.O>[OH2:11].[ClH:27].[CH2:1]([N:8]1[CH2:13][C:12]([CH2:14][CH2:15][N:46]2[CH2:45][CH2:44][C:43]([NH:42][C:40]([O:39][CH2:37][CH3:38])=[O:41])([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH2:48][CH2:47]2)([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=2)[O:11][CH2:10][C:9]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 195913894-Benzyl-6-(3,4-dichlorophenyl)-6-[2-(methanesulfonyloxy)ethyl]morpholin-3-oneHCID 212005354-(Ethoxycarbonylamino)-4-phenylpiperidine trifluoroacetate

Product 1

HCID 212006554-Benzyl-6-[2-[4-(ethoxycarbonylamino)-4-phenylpiperid-1-yl]ethyl]-6-(3,4-dichlorophenyl)morpholin-3-one hydrochloride monohydrateYield 65.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.1 g of the compound obtained in step B of EXAMPLE 14, 1 g of 4-(ethoxycarbonylamino)-4-phenylpiperidine trifluoroacetate and 0.7 g of K2CO3 in 3 ml of DMF is heated at 80-100° C. for 2 hours. After cooling to RT, the reaction mixture is poured into water and stirred for 30 minutes and the precipitate formed is wrung, washed with water and dried under vacuum at 60° C. The precipitate is chromatographed on silica H using a DCM/MeOH mixture (from 100/1; v/v to 100/4.5; v/v) as the eluent. The product obtained is dissolved in DCM, a saturated solution of hydrochloric acid in ether is added until the pH is 1, and the precipitate formed is wrung to give 0.52 g of the expected product. M.p.=148-150° C.

Workup

  1. temperatureAfter cooling to RT
  2. customthe precipitate formed
  3. washwashed with water
  4. customdried under vacuum at 60° C
  5. customThe precipitate is chromatographed on silica H
  6. customThe product obtained
  7. customthe precipitate formed

Sources & evidence

ORD record
ord-949996d7ba8b4be18c95abe1e89cbd49
Source dataset
uspto-grants-2000_01
Patent number
US06011154

Reaction notes

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