Triethylamine → N-methylcarbamoyl 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1071991Notes

Reaction equation

HRID 1071991 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.C(N(CC)CC)C.[CH3:36][N:37]=[C:38]=[O:39]>C(Cl)Cl>[CH3:36][NH:37][C:38]([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:39]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 223910171-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 11304981N-methylcarbamoyl 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolineYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (487.6 mg, 1.306 mmoles) in methylene chloride (5 mL) at 0° C. was treated with triethylamine (0.24 mL, 1.3 equiv.) and methyl isocyanate (0.10 mL, 1.3 equiv.). The mixture was immediately allowed to warm to room temperature. After 4 hours, the mixture was evaporated and the residue partitioned between ether and 2% phosphoric acid. The organic phase was washed with 1M sodium hydroxide and brine, dried over sodium sulfate, and evaporated to give a solid foam that was triturated with hexane to give the product as a white solid (494.8 mg, 88%). 1H-NMR (CDCl3) δ 2.45 (m, 1H), 2.65-3.10 (m, 3H), 2.73 (s, 3H), 3.38 (m, 1H), 3.79 (s, 3H), 3.85 (s, 3H), 3.90 (m, 2H), 4.03 (t, 1H), 4.45 (m, 1H), 6.38 (s, 1H), 6.58 (s, 1H), 7.32 (m, 10H). Mass spec. 431.2 (MH)+. Anal. Calc. for C27H30N2O3: C-75.32, H-7.02, N-6.51. Found: C-75.04, H-7.13, N-6.35.

Workup

  1. customthe mixture was evaporated
  2. customthe residue partitioned between ether and 2% phosphoric acid
  3. washThe organic phase was washed with 1M sodium hydroxide and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give a solid foam that
  7. customwas triturated with hexane

Sources & evidence

ORD record
ord-50e808b2ab334c98a724d8cb57519652
Source dataset
uspto-grants-2005_06
Patent number
US06908931B2

Reaction notes

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