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

HRID 481527Notes

Reaction equation

HRID 481527 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]([CH3:27])([CH3:26])[C:23]#[C:24][CH3:25])[CH:19]=[CH:18][C:17]=2[O:28][CH3:29])[C@@H:9]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=O)(C)(C)C.[ClH:36].CO>CCOC(C)=O>[ClH:36].[ClH:36].[CH3:27][C:22]([C:20]1[CH:19]=[CH:18][C:17]([O:28][CH3:29])=[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:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:26])[C:23]#[C:24][CH3:25]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 70136742(2S,3S)-1-tert-Butoxycarbonyl-3-[5-(1,1-dimethyl-2-butynyl)-2-methoxybenzyl]amino-2-phenylpiperidine

Product 1

HCID 70137846(2S,3S)-3-[5-(1,1-Dimethyl-2-butynyl)-2-methoxybenzyl]amino-2-phenylpiperidine DihydrochlorideYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound 56 (73 mg, 0.15 mmol) in AcOEt (6 ml) was added an excess amount of 10% HCl-MeOH (3 ml), and stirred for 18 h. After the solvent was evaporated in vacuo, the residual solid was recrystallized from MeOH-ether to give Compound 57 (48 mg, 78%) as a white solid.

Workup

  1. customAfter the solvent was evaporated in vacuo
  2. customthe residual solid was recrystallized from MeOH-ether

Sources & evidence

ORD record
ord-bd783fa279fe4ba09a107ee0976b6a44
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Reaction notes

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