Ammonia → 1-[3-(Dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carboximidamide

HRID 526806Notes

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.[NH3:26]>C(O)C.[Cu](Cl)Cl>[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](=[NH:26])[NH2:17])=[CH:15][C:10]=2[CH2:9][O:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile hydrobromide (citalopram hydrobromide, 300 mg, 1.0 equiv), copper(II) chloride (1.5 equiv) and ammonia (2.8 equiv) in ethanol (6 mL) was heated at 80° C. for 48 h. The mixture was cooled to room temperature and concentrated to dryness to give crude product (M/Z 342 [M++H]). This material was purified by re-suspending the crude product in fresh ethanol, filtration to remove insoluble material and slow evaporation under N2 to give the title product, 90 mg (23%) of a pale yellow powder.

Workup

temperatureThe mixture was cooled to room temperature
concentrationconcentrated to dryness
customto give crude product (M/Z 342 [M++H])
customThis material was purified
filtrationthe crude product in fresh ethanol, filtration
customto remove insoluble
custommaterial and slow evaporation under N2

Sources & evidence

ORD record: ord-899fb07775f546d5b660a58333b231f7
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346777B2

Reaction notes

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