Benzoyl chloride, 3,4,5-trimethoxy- → HCID 21506638, compound

HRID 1287840Notes

Reaction equation

HRID 1287840 reaction equation
[NH2:1][CH2:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[CH2:13][CH2:14][OH:15].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[C:21](Cl)=[O:22]>N1C=CC=CC=1>[CH3:30][O:29][C:25]1[CH:24]=[C:20]([CH:19]=[C:18]([O:17][CH3:16])[C:26]=1[O:27][CH3:28])[C:21]([NH:1][CH2:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[CH2:13][CH2:14][OH:15])=[O:22]

Participants

4

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 215066211-(Aminomethyl)-3,4-dihydro-2(1H)-isoquinolineethanol

Product 1

HCID 21506638HCID 21506638, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 20.6 g. of 1-aminomethyl-2-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline and 27.6 g. of 3,4,5-trimethoxybenzoyl chloride in 130 ml. of pyridine is left to stand overnight. The thus-precipitated 1-(3,4,5-trimethoxybenzamidomethyl)-2-[2-(3,4,5-trimethoxybenzoyloxy)-ethyl]-1,2,3,4-tetrahydroisoquinoline is filtered, washed with ether, and extracted with methanol; m.p. 236°-238°. The pyridine filtrate is evaporated, the residue is taken up in chloroform and washed several times with 5% potassium bicarbonate solution. After drying and evaporation, 1-(3,4,5-trimethoxybenzamidomethyl)-2-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline is obtained in this way; m.p. 138°-140° (from ethyl acetate).

Workup

  1. filtrationThe thus-precipitated 1-(3,4,5-trimethoxybenzamidomethyl)-2-[2-(3,4,5-trimethoxybenzoyloxy)-ethyl]-1,2,3,4-tetrahydroisoquinoline is filtered
  2. washwashed with ether
  3. extractionextracted with methanol
  4. customThe pyridine filtrate is evaporated
  5. washwashed several times with 5% potassium bicarbonate solution
  6. customAfter drying
  7. customevaporation

Sources & evidence

ORD record
ord-3b544d848bd647e285c1d47862fc1f67
Source dataset
uspto-grants-1976_10
Patent number
US03985881

Reaction notes

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