4-Hydroxybenzaldehyde → HCID 22851149, 화합물

HRID 1721513노트

반응식

HRID 1721513 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+].Cl>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

참가 물질

6

반응물 4

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

생성물 1

HCID 22851149HCID 22851149, 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%. m.p. 129.5°-130° C.; α!D25 +21.2° (C 1.0, CHCl3) NMR-spectral data (δ ppm, CDCl3) 2.29 (s) 3H; 2.94 (d) 2H; 3.49 (d) 2H; 3.89 (t) 1H; 3.37 (s) 2H; 6.35-6.90 (m) 4H; 6.99 (s) 4H; 7.30 (s) 5H

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-7973c3becf6942b5b7d8de6018a30813
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05510519

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