Hydrogen Bromide → (2S,3S,6S)-6-Ethyl-3-nitro-2-phenyl-piperidine HBr salt

HRID 1244067Notes

Reaction equation

HRID 1244067 reaction equation
C(OC([N:11]1[C@@H:16]([CH2:17][CH3:18])[CH2:15][CH2:14][C@H:13]([N+:19]([O-:21])=[O:20])[C@@H:12]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)C1C=CC=CC=1.[BrH:28]>C(O)(=O)CC>[BrH:28].[CH2:17]([C@@H:16]1[NH:11][C@@H:12]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@@H:13]([N+:19]([O-:21])=[O:20])[CH2:14][CH2:15]1)[CH3:18]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 44196330HCID 44196330, compound

Product 1

HCID 44196331(2S,3S,6S)-6-Ethyl-3-nitro-2-phenyl-piperidine HBr salt

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Procedure

(2S,3S,6S)-6-Ethyl-3-nitro-2-phenyl-piperidine-1-carboxylic acid benzyl ester (40 gm; 108 mmol) was dissolved in 80 ml of 30% HBr in propionic acid at room temperature. There was a rapid evolution of gas and the desired product precipitated after 3–5 minutes. The mixture was stirred at room temperature for 16 hours. The tan solids were collected, washed with ether and dried in vacuo to afford 29 gm of the (2S,3S,6S)-6-Ethyl-3-nitro-2-phenyl-piperidine HBr salt. 1H NMR (D2O, 400 MHz) δ 7.4–7.2 (br.m, 5H), 5.25 (m, 1H), 4.95 (d), 3.65 (br.m.), 2.4–2.0 (m), 1.9–1.55 (m), 0.85 (t, 3H) ppm. Mass spectra m/z=235 (p+1).

Workup

  1. customthe desired product precipitated after 3–5 minutes
  2. customThe tan solids were collected
  3. washwashed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0061085b75e5431c8f1aa3c5191caddd
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…