4-Phenylbutanal → HCID 66616601, compound

HRID 1889697Notes

Reaction equation

[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH2:13][NH2:14])[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.[C:17]1([CH2:23][CH2:24][CH2:25][CH:26]=O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[CH2:13][NH:14][CH2:26][CH2:25][CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of (3-(4-fluorophenoxy)phenyl)methanamine (200 mg, 0.092 mmol, 1.0 eq) in methanol was added 4-phenylbutanal (136 mg, 0.92 mmol, 1.0 eq). The mixture was refluxed for 2 h, then cooled to 0° C., before adding NaBH4 (105 mg, 2.76 mmol, 3.0 eq) portion wise. The mixture was stirred for 15 minutes before being quenched with 10% aq. NaHCO3 solution. The volatiles were evaporated under reduced pressure and the aqueous solution obtained was extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the desired compound (200 mg, 62%); 1H NMR (400 MHz, CD3OD) δ 7.33-6.86 (m, 13H), 3.72-3.50 (s, 2H), 2.63-2.50 (m, 4H), 1.65-1.54 (m, 4H). MS (ESI): 350.2 (M+H)+.

Workup

temperatureThe mixture was refluxed for 2 h
custombefore being quenched with 10% aq. NaHCO3 solution
customThe volatiles were evaporated under reduced pressure
customthe aqueous solution obtained
extractionwas extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-be5a3eee4cbb468e955afe61549cd3bd
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501992B2

Reaction notes

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