Acetic Anhydride → N-acetyl 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1071989Notes

Reaction equation

HRID 1071989 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.[C:36](OC(=O)C)(=[O:38])[CH3:37]>C(Cl)Cl.CCOCC>[C:36]([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:38])[CH3:37]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 223910171-(2,2-Diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 9909783N-acetyl 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolineYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1-(2,2-diphenyleth-1-yl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (1.8942 g, 5.0720 mmoles) in methylene chloride (15 mL) at 0° C. was treated with triethylamine (0.707 mL, 1.5 equiv.) and acetic anhydride (0.844 mL, 1.5 equiv.). After 2 hours at room temperature, The mixture was diluted with ether and washed with 1M sodium hydroxide (2×), water, and brine. The organic phase was dried over sodium sulfate and evaporated to give the product as a colorless foam (2.0178 g, 96%). 1H-NMR (CDCl3) δ (approx. 1.8:1 ratio of rotomers) 1.65 (rotomer A, s, 3H), 1.96 (rotomer B, s, 3H), 2.35 (rotomer B, m, 1H), 2.54 (rotomer A, m, 1H), 2.67 (rotomer A, m, 1H), 2.80 (rotomers A & B, m, 1H), 2.94 (rotomer A, m, 1H), 3.21 (rotomer A, m, 1H), 3.43 (rotomers A & B, m, 1H), 3.77 (rotomer B, s, 3H), 3.88 (rotomers A & B, s, 3H), 3.92 (rotomer A, s, 3H), 4.03 (rotomer A, m, 1H), 4.12 (rotomer B, t, 1H), 4.60 (rotomer B, m, 1H), 5.68 (rotomer A, m, 1H), 6.38 (rotomer B, s, 1H), 6.53 (rotomer A, s, 1H), 6.60 (rotomer B, s, 1H), 6.62 (rotomer A, s, 1H), 7.32 (rotomers A & B, m, 10H). Mass spec. 416.4 (MH)+. Anal. Calc. for C27H29NO3-2/3H2O: C-75.85, H-7.15, N-3.28. Found: C-75.89, H-7.03, N-3.24.

Workup

  1. washwashed with 1M sodium hydroxide (2×), water, and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-dd3be0205a8343068aa8d5c70eec4ef9
Source dataset
uspto-grants-2005_06
Patent number
US06908931B2

Reaction notes

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