Pyrrolidine → 1-[1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-yl]-1-(pyrrolidin-1-yl)-methanimine

HRID 526810Notes

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

Participants

Reactant 2

HCID 31268Pyrrolidine

HCID 77995Citalopram Hydrobromide

Product 1

HCID 1178442681-[1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-yl]-1-(pyrrolidin-1-yl)-methanimineYield 40%

Conditions

Temperature: 80 °C

Procedure

Using 100 mg of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide (citalopram HBr) and pyrrolidine (1.2 equiv) gave, after heating at 80° C. for 14 h, title product (58 mg, 40% yield) as a light yellow solid.

Workup

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Sources & evidence

ORD record: ord-4349dc7486164fc99f9798f0922aef7b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346777B2

Reaction notes

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