Hydrochloric Acid → HCID 11561089, compound

HRID 908981Notes

Reaction equation

HRID 908981 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:11])[CH2:5][CH2:4]1.[ClH:30].CCOCC>CC(CC)=O.C(O)C>[ClH:30].[CH3:29][N:2]([CH3:1])[C:3]1([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:8][CH2:7][CH:6]([CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:11])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 11561090HCID 11561090, compound

Product 1

HCID 11561089HCID 11561089, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The more polar diastereoisomer of 2-[4-dimethylamino-4-(4-fluorophenyl)cyclohexyl]-N-(3-phenylpropyl)acetamide (295 mg, 0.74 mmol) was dissolved in a mixture of ethyl methyl ketone (10 ml) and ethanol (10 ml), 5 M propanolic hydrochloric acid (0.22 ml, 1.1 mmol) was added and the mixture was stirred at RT for 1.5 h. After addition of ether (50 ml), the mixture was stirred for 2 h and the hydrochloride which had precipitated out was separated off. The product was obtained in a yield of 67% (213 mg) (Example 43).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 2 h
  3. customthe hydrochloride which had precipitated out
  4. customwas separated off
  5. customThe product was obtained in a yield of 67% (213 mg) (Example 43)

Sources & evidence

ORD record
ord-06a5c954b77e4e68b0b261ded093476c
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

Loading…