4-Hydroxybenzaldehyde → HCID 22860522, 화합물

HRID 488177노트

반응식

HRID 488177 반응식
[C:1]1([C@H:7]([NH2:16])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.[BH4-].[Na+].[ClH:28]>C(O)C>[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:16][C@@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=2)=[CH:20][CH:19]=1.[ClH:28]

참가 물질

6

반응물 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10138221(R)-alpha-Phenyl-4-methylphenethylamine

생성물 1

HCID 22860522HCID 22860522, 화합물수율 64.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

21.13 g (0.1 mole) of (R)-(-)-α-phenyl-β-p-tolylethylamine (optical purity: 100%) and 12.82 g (0.105 mole) of p-hydroxybenzaldehyde were dissolved in 750 ml of ethyl alcohol. The reaction solution thus obtained was stirred at room temperature for 3 hours, and then stirred under reflux for 1 hour. Thereafter, the reaction solution was admixed at room temperature with 1.89 g (0.05 mole) of sodium borohydride, stirred for 3 hours, and then stirred under reflux for 1 hour. The reaction mixture was admixed with 75 ml of a 10% hydrochloric acid, and then concentrated under reduced pressure to give a crude (R)-(+)-N-p-hydroxybenzyl-α-phenyl-β-p-tolylethylamine·HCl salt, which was thereafter neutralized with an aqueous sodium hydroxide solution. The resultant solution was concentrated under reduced pressure to obtain the crystals, which were then recrystallized from ethyl alcohol, so that 20.47 g of (R)-(+)-N-p-hydroxybenzyl-α-phenyl-β-p-tolylethylamine were obtained as colorless crystals. Yield: 64.5%.

후처리

  1. customThe reaction solution thus obtained
  2. stirringstirred
  3. temperatureunder reflux for 1 hour
  4. stirringstirred for 3 hours
  5. stirringstirred
  6. temperatureunder reflux for 1 hour
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d829edc27d1f44b6a001e63fc7df375e
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05298660

반응 노트

불러오는 중…