Triethylamine → HCID 53662264, compound

HRID 1720323Notes

Reaction equation

HRID 1720323 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH:18]([CH2:19][O:20][CH3:21])[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[NH:10][C:9]=2[CH2:8][NH:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.C(OCl)(C)(C)C>C1(C)C=CC=CC=1.ClCCl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 545410741,2,3,4-Tetrahydro-5-(2-chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Product 1

HCID 53662264HCID 53662264, compoundYield 33.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

1 g (0.0024 mol) of 1,2,3,4-tetrahydro-5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester is mixed in a mixture of 20 ml of toluene and 7 ml of dichloromethane at -15° C. with 1.2 ml of triethylamine. Then 0.9 ml (0.0074 mol) of tert.butylhypochlorite, dissolved in 12 ml of dichloromethane, is instilled. The reaction mixture is stirred at room temperature for two more hours. The evaporation residue is chromatographed on silica gel with equal parts of acetone and dichloromethane and yields 0.33 g (33% of theory) of 5-(2-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carboxylic acid ethyl ester, melting point 182°-184° C. (from ethanol).

Workup

  1. customThe evaporation residue is chromatographed on silica gel with equal parts of acetone and dichloromethane

Sources & evidence

ORD record
ord-3332e4d99bd34a488c8ca6e37219bbb0
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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