Hydrochloric Acid → 1-{2-[4-(2-Hydroxy-2-methylpropyl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl}cyclohexanol dihydrochloride

HRID 1987010Notes

Reaction equation

HRID 1987010 reaction equation
[OH:1][C:2]([CH3:31])([CH3:30])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH:11]([C:23]2([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[CH2:6][CH2:5]1.[ClH:32].C(OCC)C>CO>[ClH:32].[ClH:32].[OH:1][C:2]([CH3:31])([CH3:30])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH:11]([C:23]2([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 111666921-{2-[4-(2-Hydroxy-2-methylpropyl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl}cyclohexanol

Product 1

HCID 688555091-{2-[4-(2-Hydroxy-2-methylpropyl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl}cyclohexanol dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1-{2-[4-(2-hydroxy-2-methylpropyl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl}cyclohexanol (30 mg) was dissolved in methanol (0.5 mL) and treated with a saturated methanolic solution of hydrochloric acid (0.5 mL) followed by diethyl ether. After crystallizing in the refrigerator for 16 h, the resulting solid was collected, washed with diethyl ether and dried in vacuo to yield 16 mg (54%) (1-{2-[4-(2-hydroxy-2-methylpropyl)piperazin-1-yl]-1-[3-(trifluoromethoxy)phenyl]ethyl}cyclohexanol dihydrochloride as a white solid. MS m/z 445; HRMS: calcd for C23H35F3N2O3+H+, 445.26725; found (ESI, [M+H]+), 445.268.

Workup

  1. customAfter crystallizing in the refrigerator for 16 h
  2. customthe resulting solid was collected
  3. washwashed with diethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-011aa407819a460e9cd613b9287df776
Source dataset
uspto-grants-2009_06
Patent number
US07550456B2

Reaction notes

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