Hydrochloric Acid → HCID 4722253, compound

HRID 2393290Notes

Reaction equation

[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:9]([O:16][C:17]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>O.C(O)C>[CH2:1]([NH:8][CH2:19][C:18]1[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH3:26])[C:17]=1[O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

Conditions

Temperature: 5 °C

Procedure

Ethyl alcohol (30 ml) and n-heptylamine (5.23 g, 45.4 mmol) were added to 2-benzyloxy-3-methoxybenzaldehyde (10 g, 41.3 mmol), and the mixture was heated with stirring under reflux for 2 hours. The reaction mixture was cooled to 5° C., added with sodium borohydride (2.34 g, 61.9 mmol), and then stirred at room temperature for 10 hours. The reaction mixture was added with water (10 ml) and aqueous 6N hydrochloric acid to decompose excess sodium borohydride, and then made alkaline with 25% aqueous sodium hydroxide and extracted with toluene. After the extract was washed with saturated brine and dried over anhydrous sodium sulfate, the solvent was evaporated to give N-heptyl-(2-benzyloxy-3-methoxyphenyl)methylamine (13.5 g) as oil.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 2 hours
stirringstirred at room temperature for 10 hours
extractionextracted with toluene
washAfter the extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated

Sources & evidence

ORD record: ord-c502a8ea26c040bbb552616b1c52f13e
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05807860

Reaction notes

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