Benzoyl chloride, 3,4,5-trimethoxy- → 5,6,13,13a-tetrahydro-2,3,11-trimethoxy-10-(3', 4', 5'-trimethoxybenzoxy)-8H-dibenzo-[a, g]quinolizine

HRID 1580596Notes

Reaction equation

HRID 1580596 reaction equation
Cl.[OH:2][C:3]1[C:4]([O:25][CH3:26])=[CH:5][C:6]2[CH2:15][CH:14]3[N:9]([CH2:10][CH2:11][C:12]4[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:13]=43)[CH2:8][C:7]=2[CH:24]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39])[C:32](Cl)=O>N1C=CC=CC=1>[CH3:23][O:22][C:17]1[C:18]([O:20][CH3:21])=[CH:19][C:12]2[CH2:11][CH2:10][N:9]3[CH:14]([CH2:15][C:6]4[CH:5]=[C:4]([O:25][CH3:26])[C:3]([O:2][CH2:32][C:31]5[CH:35]=[C:36]([O:40][CH3:41])[C:37]([O:38][CH3:39])=[C:29]([O:28][CH3:27])[CH:30]=5)=[CH:24][C:7]=4[CH2:8]3)[C:13]=2[CH:16]=1

Participants

4

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 8673298310-hydroxy-2,3,11-trimethoxy-5,6,13,13a-tetrahydro-8H-dibenzo[a, g]quinolizine hydrochloride

Product 1

HCID 867329865,6,13,13a-tetrahydro-2,3,11-trimethoxy-10-(3', 4', 5'-trimethoxybenzoxy)-8H-dibenzo-[a, g]quinolizineYield 45.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.9 g of 10-hydroxy-2,3,11-trimethoxy-5,6,13,13a-tetrahydro-8H-dibenzo[a, g]quinolizine hydrochloride was treated in the same manner as described in Example 6, using 2.0 g of 3,4,5-trimethoxybenzoyl chloride and 200 ml of anhydrous pyridine and there was obtained 1.2 g (44.4% yield) of 5,6,13,13a-tetrahydro-2,3,11-trimethoxy-10-(3', 4', 5'-trimethoxybenzoxy)-8H-dibenzo-[a, g]quinolizine as a pale yellow powder. The methiodide derived from this compound was found to be in agreement with the methiodide of the compound obtained in Example 3 as determined from the melting point and IR spectrum.

Sources & evidence

ORD record
ord-049deb0585944dffb928ba29668458b4
Source dataset
uspto-grants-1976_01
Patent number
US03933826

Reaction notes

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