Sodium Bicarbonate → (5-Methyl-2-(pent-4-enyl)phenyl)methanamine

HRID 501716Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14])=[C:6]([CH:9]=1)[CH:7]=O.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+].C(=O)(O)[O-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][CH2:12][CH:13]=[CH2:14])=[C:6]([CH2:7][NH2:21])[CH:9]=1

Participants

Conditions

Temperature: 65 °C

Procedure

Step AI (5): 5-Methyl-2-(pent-4-enyl)benzaldehyde (170 mg, 0.90 mmol) and ammonium acetate (10.44 g, 135.5 mmol) was dissolved in methanol (35 mL). Sodium cyanoborohydride (341 mg, 5.42 mmol) was added. The reaction mixture was stirred at 65° C. in a high-pressure vessel for 1 h. Aqueous sodium bicarbonate solution was added and the reaction mixture was extracted with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by reverse phase chromatography to give (5-methyl-2-(pent-4-enyl)phenyl)methanamine (57 mg, 33%) as a colorless oil. LC-MS (M+H)+=190.09.

Workup

extractionthe reaction mixture was extracted with DCM
dry with materialThe combined organic phases were dried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuum
customThe residue was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-4ec2339cf25f476e8f50143bf52c5277
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772221B2

Reaction notes

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