Hydrochloric Acid → HCID 86748916, compound

HRID 1757239Notes

Reaction equation

HRID 1757239 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH3:24])[C@@H:10]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O)(C)(C)C>C(OCC)(=O)C>[ClH:1].[CH3:24][C:18]1[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C@H:11]1[CH2:12][CH2:13][CH2:14][NH2+:9][C@H:10]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 53677701HCID 53677701, compound

Product 1

HCID 86748916HCID 86748916, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Ethyl acetate (10 ml) was saturated with hydrogen chloride by passing HCl gas for 5 min and a solution of 0.254 g of (2S,3S)-1-t-butoxycarbonyl-3-((2,3-dimethylphenyl)methoxy)-2-phenylpiperidine (prepared according to Description 3d) in 7 ml of ethyl acetate was added. After stirring for 2 h, the reaction mixture was concentrated in vacuo. The residual white solid was washed with ether, filtered and dried to obtain 0.23 g of (2S,3S)-3-((2,3-dimethylphenyl)methyloxy)-2-phenylpiperidinium hydrochloride. 1H NMR (DMSO-d6) δ1.6-1.9 (3H, m), 1.75 (3H, s), 2.15 (3H, s), 2.2 (1H, m), 3.05 (1H, m), 3.25 (1H, m), 3.84 (1H, s), 4.05 (1H, d, J=14 Hz), 4.45 (1H, d, J=14 Hz), 4.48 (1H, s), 6.95-7.5 (8H, m), 8.8 (1H, br s), 9.4 (1H, br s).

Workup

  1. customfor 5 min
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. washThe residual white solid was washed with ether
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-5e49f1dee13f464d830518a1dbe2c026
Source dataset
uspto-grants-1995_08
Patent number
US05444074

Reaction notes

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