Triethylamine → N-cycloheptyl-5-[benzyl(2-chloroethyl)amino]pentanamide

HRID 610775Notes

Reaction equation

CS([Cl:5])(=O)=O.[CH:6]1([NH:13][C:14](=[O:30])[CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:21]O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C(N(CC)CC)C>ClCCl>[CH:6]1([NH:13][C:14](=[O:30])[CH2:15][CH2:16][CH2:17][CH2:18][N:19]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:20][CH2:21][Cl:5])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

Conditions

Temperature: 20 °C

Procedure

Methanesulfonyl chloride (0.78 g, 0.52 ml, 6.6 mmole) is added dropwise with stirring to a cooled solution of N-cycloheptyl-5-[benzyl(2-hydroxyethyl)amino]pentanamide (2.14 g, 6 mmole) in dichloromethane (20 ml) in the presence of triethylamine (0.69 g, 0.94 ml, 6.6 mmole). Agitation is maintained for 18 hours at 20° C. The reaction mixture is filtered with iced water (25 ml) then dried over magnesium sulfate. Filtration and evaporation of the solvent under reduced pressure give 2.2 g (98%) of the desired compound in the form of an oil.

Workup

filtrationThe reaction mixture is filtered with iced water (25 ml)
dry with materialthen dried over magnesium sulfate
filtrationFiltration and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-ad769e8ded184b9ca87d1d74bdef8ed9
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05998666

Reaction notes

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