1-t-Butoxycarbonyl-4-(3-(3,5-difluorophenyl)propyl) piperidine → 4-(3-(3,5-Difluorophenyl)propyl)piperidine

HRID 1386745Notes

Reaction equation

HRID 1386745 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>Cl.CO>[F:24][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][CH2:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:22]=[C:21]([F:23])[CH:20]=1

Participants

4

Reactant 1

HCID 211806591-t-Butoxycarbonyl-4-(3-(3,5-difluorophenyl)propyl) piperidine

Product 1

HCID 211806144-(3-(3,5-Difluorophenyl)propyl)piperidineYield 70%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1-t-butoxycarbonyl-4-(3-(3,5-difluorophenyl)propyl)piperidine (from EXAMPLE 95, Step D) in 2.0 N HCl in MeOH was stirred at rt for 20 h. The solution was concentrated. Ether was added and the mixture was concentrated to remove excess HCl to afford 381 mg (70% yield from EXAMPLE 95, Step C) of the title compound: 1H NMR (500 MHz, CD3OD) δ 1.32-1.37 (4H), 1.64-1.68 (1H), 1.94 (d, J=14.2, 2H), 2.64 (t, J=7.3, 2H), 2.95 (t, J=13.1, 2H), 3 35 (d, J=12.6, 2H), 6.69-6.78 (m, 1H). 6.80 (d, J=8.2, 2H).

Workup

  1. concentrationThe solution was concentrated
  2. additionEther was added
  3. concentrationthe mixture was concentrated
  4. customto remove excess HCl

Sources & evidence

ORD record
ord-89c15acd128948e7b09d01d3211c065b
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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