Benzaldehyde → 4-(2-(Benzylamino)ethyl)phenol

HRID 130687

반응식

HRID 130687 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[CH2:1]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 5610TyramineHCID 4311764Sodium borohydride

생성물 1

HCID 30425724-(2-(Benzylamino)ethyl)phenol수율 61%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Add benzaldehyde (7.5 mL, 74 mmol) to a stirred solution of tyramine (10.00 g, 73 mmol) and anhydrous methanol (90 mL). Bleat reaction to reflux for 1 h under nitrogen. Cool reaction to 0° C. and slowly add sodium borohydride (2.84 g, 75 mmol). Stir for 1 h at room temperature and then concentrate on a rotary evaporator. Add water (100 mL) and stir for 1.5 h at room temperature. Filter and wash with water to yield 10.11 g (61%) of 4-(2-benzylamino-ethyl)-phenol: mass spectrum (ion spray): m/z=228.1 (M+1); 1H NMR (DMSO-d6): 9.14 (br s, 1H), 7.29-7.18 (m, 5H), 6.96 (d, 2H), 6.65 (d, 2H), 3.69 (s, 2H), 2.67-2.60 (m, 4H), 2.02 (br s, 1H).

후처리

  1. customBleat reaction
  2. temperatureto reflux for 1 h under nitrogen
  3. temperatureCool
  4. customreaction to 0° C.
  5. concentrationconcentrate on a rotary evaporator
  6. stirringAdd water (100 mL) and stir for 1.5 h at room temperature
  7. filtrationFilter
  8. washwash with water

출처 및 근거

ORD 기록
ord-60da40f474f24df0ad7fdcfcbf3d0634
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381719B2

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