3-(4-Methoxyphenyl)propan-1-amine → HCID 20481274, compound

HRID 1648887Notes

Reaction equation

HRID 1648887 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[ClH:13].NCCC1C=CC(OC)=C2C=1[CH2:19][C:20](=[O:28])[NH:21]2>>[ClH:13].[NH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]2[C:5]=1[CH2:19][C:20](=[O:28])[NH:21]2

Participants

3

Reactant 2

HCID 30298153-(4-Methoxyphenyl)propan-1-amineHCID 20481280HCID 20481280, compound

Product 1

HCID 20481274HCID 20481274, compound

Procedure

Using 50 g of p-methoxyphenylpropylamine for the starting material of Example 1 gives 4-(3-aminopropyl)-7-methoxy-2(3H)-indolone hydrochloride. This material (3 g) was converted to the base and alkylated using methyl formate-formaldehyde at reflux to give 4-(3-dimethylaminopropyl)-7-methoxy-2(3H)-indolone hydrochloride and, after treatment with boron tribromide in methylene chloride at -20°, 4-(3-dimethylaminopropyl)-7-hydroxy-2(3H)-indolone hydrobromide.

Sources & evidence

ORD record
ord-e5507ed22db141bdaf415e9269b78ce3
Source dataset
uspto-grants-1983_11
Patent number
US04414224

Reaction notes

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