Triethylamine → HCID 19004138, compound

HRID 2226048Notes

Reaction equation

[C:1]1([N:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH:11]2[CH2:16][CH2:17][OH:18])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:32]([N:37]([CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:38](Cl)=[O:39])[CH2:33][CH2:34][CH2:35][CH3:36]>O1CCCC1>[C:19]1([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:38](=[O:39])[N:37]([CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:12][CH:11]2[CH2:16][CH2:17][OH:18])=[O:9])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 174 mg (0.53 mmol) of (RS)-1-(N,N-diphenylcarbamoyl)-2-(2-hydroxyethyl) piperazine in 10 mL of dry tetrahydrofuran was added 450ml (3.23 mmol) of triethylamine in one portion and 176 mg (0.80 mmol) of dipentylcarbamyl chloride (dissolved in 2 mL of dry tetrahydrofuran) and the mixture was stirred under nitrogen at 60° C. for two days. The solution was cooled and concentrated in vacuo. Flash chromatography on 25 g of silica gel using 75:25 v/v ethyl acetate/hexane as the eluant afforded 173 mg (64%) of a yellow oil.

Workup

temperatureThe solution was cooled
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-90da6f639671472b8d1552e07fe7306c
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344830

Reaction notes

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