Urea → 1-(2,2-Diphenyl-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid amide

HRID 1071990노트

반응식

HRID 1071990 반응식
[C:1]1([CH:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH2:12][CH2:11][NH:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:29][C:30](N)=[O:31]>>[C:30]([N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH:9]1[CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:31])[NH2:29]

참가 물질

3

반응물 2

HCID 1176Urea2회HCID 223910171-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 112470501-(2,2-Diphenyl-ethyl)-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid amide

실험 절차

A solution of 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1.0598 g, 2.838 mmoles) and urea (1.704 g, 10 equiv.) was heated at reflux. After 3 hours, TLC indicated less than 15% conversion. More urea (15.5 g, 90 equiv.) was added. Reflux continued for 24 hours. The solvent was then evaporated and the residue dissolved in water (80 mL). A white solid formed. After 1 hour, the solid was collected by filtration, washed with water, and dried in vacuo overnight (1.0554 g, 89%). 1H-NMR (CDCl3) δ 2.49 (m, 1H), 2.69 (m, 2H), 2.90 (m, 1H), 3.37 (m, 1H), 3.82 (s, 3H), 3.86 (s, 3H), 3.89 (m, 2H), 4.05 (t, 1H), 4.38 (m, 1H), 6.41 (s, 1H), 6.60 (s, 1H), 7.29 (m, 10H). Mass spec. 417.3 (MH)+. Anal. Calc. for C26H28N2O3: C-74.98, H-6.78, N-6.73. Found: C-74.72, H-6.74, N-6.45.

후처리

  1. temperatureat reflux
  2. temperatureReflux
  3. waitcontinued for 24 hours
  4. customThe solvent was then evaporated
  5. dissolutionthe residue dissolved in water (80 mL)
  6. customA white solid formed
  7. waitAfter 1 hour
  8. filtrationthe solid was collected by filtration
  9. washwashed with water
  10. customdried in vacuo overnight (1.0554 g, 89%)

출처 및 근거

ORD 기록
ord-8ed5401d42754f188ce6e0017c1c2b7d
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908931B2

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