Benzylethanolamine → N-cyclohepty-5-[benzyl(2-hydroxyethyl)amino]pentanamide

HRID 610774Notes

Reaction equation

[CH:1]1([NH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13]Br)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:16]([NH:23][CH2:24][CH2:25][OH:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1([NH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][N:23]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:24][CH2:25][OH:26])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

N-cycloheptyl-5-bromopentanamide (4.15 g, 15 mmole) in solution in dimethylformamide (20 ml) is added dropwise to a hot solution (60° C.) of N-benzylethanolamine (2.27 g, 2.13 ml, 15 mmole) in dimethylformamide (25 ml) in the presence of potassium carbonate (4.15 g, 3 mmole). The reaction mixture is agitated for 2 hours at 60° C. then the solvent is evaporated under reduced pressure. The residue is taken up in dichloromethane (50 ml) and washed with water (3×30 ml). The organic phase is collected, dried over magnesium sulfate; the solvent is evaporated under reduced pressure. The product obtained is purified by flash chromatography over silica gel in a mixture of dichloromethane/methanol (90/10) to give 3.04 g (50%) of the expected compound in the form of an oil.

Workup

customthe solvent is evaporated under reduced pressure
washwashed with water (3×30 ml)
customThe organic phase is collected
dry with materialdried over magnesium sulfate
customthe solvent is evaporated under reduced pressure
customThe product obtained
customis purified by flash chromatography over silica gel in a mixture of dichloromethane/methanol (90/10)

Sources & evidence

ORD record: ord-fadcc4f3ec5f43bab5e96e01299add98
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998666

Reaction notes

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