Benzylamine → HCID 178483386, compound

HRID 526808Notes

Reaction equation

Br.[CH3:2][N:3]([CH3:25])[CH2:4][CH2:5][CH2:6][C:7]1([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:11]2[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][C:10]=2[CH2:9][O:8]1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([NH:33][C:16]([C:14]1[CH:13]=[CH:12][C:11]2[C:7]([CH2:6][CH2:5][CH2:4][N:3]([CH3:25])[CH3:2])([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[O:8][CH2:9][C:10]=2[CH:15]=1)=[NH:17])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Reactant 2

HCID 7504Benzylamine

HCID 77995Citalopram Hydrobromide

Product 1

HCID 178483386HCID 178483386, compoundYield 19%

Conditions

Temperature: 80 °C

Procedure

Using 250 mg of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide (citalopram HBr) and benzylamine (1.2 equiv) gave, after heating at 80° C. for 14 h, title product (72 mg, 19% yield) as a white solid.

Workup

customgave

Sources & evidence

ORD record: ord-3c7e2bb821384e6bb12e091912f90ffb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346777B2

Reaction notes

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