Benzoyl chloride, 3,4,5-trimethoxy- → Benzamide, N-(1,2,3,4-tetrahydro-2-methylisoquinolin-5-yl)-3,4,5-trimethoxy-

HRID 2397931Notes

Reaction equation

HRID 2397931 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19].C(=O)(O)[O-].[K+]>C1C=CC=CC=1>[CH3:27][O:26][C:22]1[CH:21]=[C:17]([CH:16]=[C:15]([O:14][CH3:13])[C:23]=1[O:24][CH3:25])[C:18]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2)=[O:19]

Participants

5

Reactant 3

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516893Potassium BicarbonateHCID 141712692-Methyl-1,2,3,4-tetrahydroisoquinolin-5-amine

Product 1

HCID 213990Benzamide, N-(1,2,3,4-tetrahydro-2-methylisoquinolin-5-yl)-3,4,5-trimethoxy-Yield 52.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

5-Amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (3.76 g) was dissolved in anhydrous benzene (100 ml) and treated with 3,4,5-trimethoxybenzoyl chloride (5 g) under reflux for 16 hours in the presence of 0.25 g of anhydrous potassium bicarbonate. The precipitated solid was filtered and washed with sodium carbonate solution. The solid was recrystallized from benzene to yield 4.04 g of fine needles; mp 142.8-143.1° C.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with sodium carbonate solution
  3. customThe solid was recrystallized from benzene

Sources & evidence

ORD record
ord-04ca0aceeba1475babfc7a26d5c72135
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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