Hydrochloride methanol → (2S,3S)-3-[5-(1,1-Dimethyl-4,4,4-trifluoro-2-butynyl)-2-methoxybenzyl]amino-2-phenylpiperidine dihydrochloride

HRID 2269268Notes

Reaction equation

HRID 2269268 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][CH2:15][C:16]2[CH:21]=[C:20]([C:22]([CH3:30])([CH3:29])[C:23]#[C:24][C:25]([F:28])([F:27])[F:26])[CH:19]=[CH:18][C:17]=2[O:31][CH3:32])[C@@H:9]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=O)(C)(C)C.[ClH:39].CO>CCOC(C)=O>[ClH:39].[ClH:39].[CH3:30][C:22]([C:20]1[CH:19]=[CH:18][C:17]([O:31][CH3:32])=[C:16]([CH:21]=1)[CH2:15][NH:14][C@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][C@H:9]1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:29])[C:23]#[C:24][C:25]([F:28])([F:26])[F:27]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 70001735(2S,3S)-1-tert-Butoxycarbonyl-3-[5-(1,1-dimethyl-4,4,4-trifluoro-2-butynyl)-2-methoxybenzyl]amino-2-phenylpiperidine

Product 1

HCID 70000615(2S,3S)-3-[5-(1,1-Dimethyl-4,4,4-trifluoro-2-butynyl)-2-methoxybenzyl]amino-2-phenylpiperidine dihydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound 59 (34 mg, 0.064 mmol) in AcOEt (8 ml) was added an excess amount of HCl-MeOH. The mixture was stirred for 18 h and then evaporated in vacuo, the residual solid was recrystallized from MeOH-Et2O to give Compound 60 (24 mg, 75%) as a white solid.

Workup

  1. customevaporated in vacuo
  2. customthe residual solid was recrystallized from MeOH-Et2O

Sources & evidence

ORD record
ord-170c32216e1e4d14986e538791dec033
Source dataset
uspto-grants-2001_12
Patent number
US06329396B1

Reaction notes

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