Phenylmethyl 4-(4-methoxyphenyl)-1-piperidinecarboxylate → 4-(4-Methoxyphenyl)piperidine

HRID 2256030Notes

Reaction equation

HRID 2256030 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 19029132Phenylmethyl 4-(4-methoxyphenyl)-1-piperidinecarboxylate

Product 1

HCID 106792704-(4-Methoxyphenyl)piperidineYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-(4-methoxyphenyl)piperidine (0.42 g) in ethanol (5 mL) was treated with 10% palladium on carbon (0.04 g) and hydrogenated for 16 hours at atmospheric pressure. The reaction mixture was filtered through diatomaceous earth and evaporated to afford 4-(4-methoxyphenyl)piperidine as a colorless oil (0.22 g); NMR (CDCl3): 1.59-1.71 (m, 2), 1.85 (d, 2, J=12), 2.71-2.81 (d of t,2, J=12), 3.19-3.23 (broad, 2), 3.79 (s, 3), 6.83-6.87 (m, 2), 7.12-7.26 (m, 2); MS: m/z=192(M+1). This material was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customevaporated

Sources & evidence

ORD record
ord-66236a0ce5024e0aacf11080f4ee081b
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

Loading…