Hydrochloric Acid → (+/-)-1-(3,4,5-Trimethoxybenzoyl)-decahydro-8-(1-pyrrolidinyl)-quinoline hydrochloride

HRID 1073145Notes

Reaction equation

HRID 1073145 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([Cl:8])=[O:7].[N:16]1([CH:21]2[CH:30]3[CH:25]([CH2:26][CH2:27][CH2:28][NH:29]3)[CH2:24][CH2:23][CH2:22]2)[CH2:20][CH2:19][CH2:18][CH2:17]1.Cl>CCOCC>[ClH:8].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([N:29]1[CH:30]2[CH:25]([CH2:24][CH2:23][CH2:22][CH:21]2[N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:26][CH2:27][CH2:28]1)=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 13983380(+/-)-Decahydro-8-(-pyrrolidinyl)-quinoline

Product 1

HCID 86742835(+/-)-1-(3,4,5-Trimethoxybenzoyl)-decahydro-8-(1-pyrrolidinyl)-quinoline hydrochlorideYield 36.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

510 mg of 3,4,5-trimethoxybenzoyl chloride and 417 mg of the product of Step C of Example 1 were reacted in ether for 40 hours at ambient temperature and the crude product obtained in the form of the base was converted into the hydrochloride as in Example 1 to obtain 319 mg of the expected product melting at ≈260° C.

Workup

  1. customthe crude product obtained in the form of the base

Sources & evidence

ORD record
ord-3bd0ccddf938479b9428ff5a1b16cde7
Source dataset
uspto-grants-1990_11
Patent number
US04968700

Reaction notes

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