Ammonia → HCID 86758487, compound

HRID 2306159Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH:10]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22])[CH2:11][NH:12][O:13][CH3:14].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH4-].[Na+].[ClH:33].N>C(O)C>[ClH:33].[CH2:23]([N:12]([O:13][CH3:14])[CH2:11][CH:10]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:22])[CH2:9][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

0.6 g (2.0 mmol) of 3-(2,6-difluorophenyl)-methoxy-2-(2,6-dimethylphenyl)-propylamine are stirred with 0.3 g (2.8 mmol) of benzaldehyde for 1 h at 60° C. Then 10 ml of ethanol and 0.3 9 of NaBH4 are added and the mixture is stirred for 30 minutes at 50° C. It is left to cool, 10 ml of 2 N hydrochloric acid are added dropwise and the ethanol is eliminated in vacuo. The residue is combined with 10 ml of conc. ammonia and extracted twice with 30 ml of ethyl acetate. The organic phase is washed with water, dried and concentrated by evaporation in vacuo. The residue is taken up in ether and the hydrochloride is precipitated with ethereal hydrochloric acid. Yield: 0.7 g (81%), melting point: 179° C.

Workup

waitIt is left
temperatureto cool
extractionextracted twice with 30 ml of ethyl acetate
washThe organic phase is washed with water
customdried
concentrationconcentrated by evaporation in vacuo
customthe hydrochloride is precipitated with ethereal hydrochloric acid

Sources & evidence

ORD record: ord-9b23b1d00a6b4616bea882c681205161
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441237B1

Reaction notes

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