Hydrochloric Acid → HCID 69768833, compound

HRID 1978901Notes

Reaction equation

HRID 1978901 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([NH:14][CH2:15][C:16]2[CH:25]=[C:24]3[C:19]([CH2:20][CH2:21][O:22][C:23]3([CH3:30])[C:26]([F:29])([F:28])[F:27])=[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]>C(OCC)(=O)C>[ClH:39].[ClH:39].[CH3:32][O:31][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][C:16]=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:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:23]([CH3:30])([C:26]([F:29])([F:27])[F:28])[O:22][CH2:21][CH2:20]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15516312HCID 15516312, compound

Product 1

HCID 69768833HCID 69768833, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-tert-butoxycarbonyl-(2S,3S)-3-(6-methoxy-1-methyl-1-trifluoromethylisochroman-7-yl)methylamino-2-phenylpiperidine (325 mg, 0.61 mmol) in ethyl acetate (5 ml) was added a methanolic HCl solution dropwise under nitrogen at room temperature for 8 hours. The solvent was removed, and recrystallized from ethanol to give the title compound (88 mg, 28.4%). mp: 193-201° C. 1H-NMR (major isomer, free amine, CDCl3): 7.33-7.20 (m, 5H), 6.95 (s, 1H), 6.43 (s, 1 H), 4.13-4.09 (m, 1H), 3.92-3.84 (m, 2H), 3.62 (d, J=13.9 Hz, 1H), 3.51 (s, 3H), 3.33 (d, J=13.9 Hz, 1H), 3.31-3.24 (m, 1H), 2.84-2.74 (m, 4H), 2.12-2.07 (m, 1H), 1.94-1.82 (m, 1H), 1.67-1.62 (m, 1H), 1.59 (s, 3H), 1.43-1.38 (m, 1H)

Workup

  1. customThe solvent was removed
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-0cbeb3e46f7e4075ba9e5164d7688c56
Source dataset
uspto-grants-2001_05
Patent number
US06239147B1

Reaction notes

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