Benzaldehyde → HCID 67130440, compound

HRID 2380972Notes

Reaction equation

[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[CH2:23][CH2:22][O:21][CH:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19]2)=[O:17])=[CH:12][CH:11]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([N:18]2[CH2:23][CH2:22][O:21][CH:20]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:19]2)=[O:17])=[CH:14][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Benzaldehyde (0.1 ml, 1 mmol) was added to a stirred solution of (4-amino-phenyl)-(2-phenyl-morpholin-4-yl)-methanone (240 mg, 0.84 mmol) in dichloromethane (20 ml) and the resulting mixture was heated to 45° C. for 2 hours. The reaction mixture was cooled to room temperature then sodium triacetoxyborohydride (250 mg, 1.2 mmol) was added and the reaction was stirred at room temperature for 48 hours. The reaction was diluted with dichloromethane (10 ml) and quenched by the addition of water (10 ml). The aqueous was washed with dichloromethane (2×10 ml), the organics combined and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue purified by flash chromatography to afford the title compound as a colourless oil (0.22 g, 70% yield). HPLC retention time 6.18 min. Mass spectrum (ES+) m/z 373 (M+H).

Workup

temperatureThe reaction mixture was cooled to room temperature
customquenched by the addition of water (10 ml)
washThe aqueous was washed with dichloromethane (2×10 ml)
dry with materialdried over magnesium sulfate
concentrationThe solvent was concentrated in vacuo
customthe residue purified by flash chromatography

Sources & evidence

ORD record: ord-f5ab1bcc404943febf9e27fe2f543b01
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258138B2

Reaction notes

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