1,3-Dibenzyl-4-hydroxypiperidine → 4-Hydroxy-3-benzylpiperidine

HRID 396328노트

반응식

HRID 396328 반응식
C([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)C1C=CC=CC=1>CO.[H][H].[OH-].[Pd+2].[OH-]>[OH:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 1

HCID 230037131,3-Dibenzyl-4-hydroxypiperidine

생성물 1

HCID 230036754-Hydroxy-3-benzylpiperidine

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매HCID 178418361HCID 178418361, 화합물용매

실험 절차

A mixture of 1,3-dibenzyl-4-hydroxypiperidine (1.7 g, 6.0 mmole) and 20% palladium hydroxide (0.3 g) in methanol (20 ml) was stirred in hydrogen atmosphere (1 atm.) for 12 hr at 35° C. Catalyst was filtered off, washed with methanol, filtrate was concentrated to dryness to give 4-hydroxy-3-benzylpiperidine as oil. Yield 1.0 g (91%), C12H17NO, m/z 192 (M+1) PMR (CDCl3): 1.66 (1H, m, H3), 1.94 (1H, m, H5), 2.26 (2H, m, H5, & OH, D2O exchangeable), 2.62 (1H, m, H2), 2.74 (1H, m, H6), 3.02 (1H, m, H2), 3.34 (1H, m, H6), 3.52 (1H, bs, NH, D2O exchangeable), 3.9 (1H, m, H4), 4.74 (2H, m, CH2-Ar), 7.28 (5H, m, ArH).

후처리

  1. filtrationCatalyst was filtered off
  2. washwashed with methanol, filtrate
  3. concentrationwas concentrated to dryness

출처 및 근거

ORD 기록
ord-fbf4a62d9d524262b8f37191a528f44d
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608078B2

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