Ethyl chloroacetate → HCID 24823447, compound

HRID 1274978Notes

Reaction equation

HRID 1274978 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.Cl[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 24823447HCID 24823447, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-methoxy-1,2,3,4-tetrahydroisoquinoline, Sall and Grunewald, J. Med. Chem. 1987, 30, 2208-2216 (1.1 mmol), ethyl chloroacetate (1.17 mmol), and K2CO3 (1.17 mmol) in CH3CN (10 mL) is stirred for 18 h. The mixture is partitioned between EtOAc and H2O. The organic phase is concentrated to an oil, which is purified by chromatography (silica gel, gradient, 20-80% EtOAc/hexane) to afford the title compound.

Workup

  1. customThe mixture is partitioned between EtOAc and H2O
  2. concentrationThe organic phase is concentrated to an oil, which
  3. customis purified by chromatography (silica gel, gradient, 20-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-df87d5cf47fe414eb289fc72d71208b1
Source dataset
uspto-grants-2000_12
Patent number
US06159964

Reaction notes

Loading…