Water → N1-(4-Chlorophenyl)-N2-[[4-(1,1-dimethylethyl)phenyl]methyl]-N1-methyl-1,2-ethanediamine

HRID 855237노트

반응식

HRID 855237 반응식
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:24])[CH2:21][CH2:22][NH2:23])=[CH:16][CH:15]=1.[BH4-].[Na+].O>CO>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH:23][CH2:22][CH2:21][N:20]([C:17]2[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=2)[CH3:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 703244-tert-ButylbenzaldehydeHCID 88988N-(4-Chlorophenyl)-N-methylethylenediamineHCID 4311764Sodium borohydride

생성물 1

HCID 68578813N1-(4-Chlorophenyl)-N2-[[4-(1,1-dimethylethyl)phenyl]methyl]-N1-methyl-1,2-ethanediamine수율 90%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1.62 g (10 mmol) of 4-tert-butyl benzaldehyde and 1.85 g (10 mmol) of N-(4-chloro -phenyl)-N-methyl-ethane-1,2-diamine were dissolved in 20 ml methanol and the solution was stirred for 2 h at rt. 567 mg (15 mmol) of sodium borohydride were added in portions under nitrogen. The reaction mixture was stirred at rt over night. Water was added and the solvent was evaporated. The reaction mixture was extracted with diethyl ether and the organic layer was washed with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated to leave the 2.97 g (90%) product as a yellow oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.34 (d, 2H), 7.24 (d, 2H), 7.13 (d, 2H), 6.64 (d, 2H), 3.77 (s, 2H), 3.42 (t, 2H), 2.91 (s, 3H), 2.83 (t, 2H), 1.30 (s, 9H).

후처리

  1. stirringThe reaction mixture was stirred at rt over night
  2. customthe solvent was evaporated
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. washthe organic layer was washed with saturated aqueous NaCl solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-b018923e6f1a4f08a52df0d9566bfdb7
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259183B2

반응 노트

불러오는 중…