Hydrochloric Acid → HCID 19824141, compound

HRID 1769822Notes

Reaction equation

[CH:1]([NH:3][C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[ClH:26]>O1CCCC1.C(OCC)(=O)C.C(O)(C)C>[ClH:26].[CH3:1][NH:3][C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 35 °C

Procedure

N-formyl-1,2-diphenyl-2-propylamine (23.6 g, 0.1 mol) was added to a stirred suspension of LiAlH4 (15.0 g, 0.395 mol) in 1 L of dry tetrahydrofuran. After 2 hours the mixture was heated at 35° C. for 22 hours, then refluxed for 2 hours, and allowed to cool to room temperature. Water was added to decompose the excess LiAlH4, and the mixture filtered to remove the solid salts. Evaporation of the solvent gave 23.0 g of the crude product as a yellow oil. This was dissolved in 180 ml of ethyl acetate and 20 ml of isopropanol and acidified with HCl gas. Upon standing a white solid crystallized which was collected by filtration and vacuum dried at 65° C. to give 21.7 g (84%) of N-methyl-1,2-diphenyl-2-propylamine hydrochloride, mp 200°-201° C.

Workup

temperaturerefluxed for 2 hours
temperatureto cool to room temperature
filtrationthe mixture filtered
customto remove the solid salts
customEvaporation of the solvent
customgave 23.0 g of the crude product as a yellow oil
customcrystallized which
filtrationwas collected by filtration and vacuum
customdried at 65° C.

Sources & evidence

ORD record: ord-437314d65d91461b9f996248bc3bc2d1
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05382683

Reaction notes

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