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

HRID 1071990Notes

Reaction equation

HRID 1071990 reaction equation
[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]

Participants

3

Reactant 2

HCID 1176Urea2×HCID 223910171-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

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

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-8ed5401d42754f188ce6e0017c1c2b7d
Source dataset
uspto-grants-2005_06
Patent number
US06908931B2

Reaction notes

Loading…