Triethylamine → Ethyl [2-[4-(4-bromophenyl)-1-piperazinyl]-ethyl]carbamate

HRID 1975877Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:15][CH2:16][NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1-(4-bromophenyl)piperazine (0.018 mol) and ethyl (2-chloroethyl)-carbamate (0.036 mol) was stirred for 2 hours at 130° C. Triethylamine (3 ml) was added and the mixture was stirred for 15 minutes at 130° C. The reaction mixture was cooled to room temperature, CH2Cl2 was added and the resulting mixture was washed with water. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 4.3 g (67.2 %) of ethyl [2-[4-(4-bromophenyl)-1-piperazinyl]-ethyl]carbamate (interm. 1).

Workup

stirringthe mixture was stirred for 15 minutes at 130° C
temperatureThe reaction mixture was cooled to room temperature
washthe resulting mixture was washed with water
customThe organic layer was separated
customdried
filtrationfiltered
customthe solvent was evaporated
customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
customThe pure fractions were collected
customthe solvent was evaporated

Sources & evidence

ORD record: ord-089ed39a282c45bb869fd437f0f1d631
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06224849B1

Reaction notes

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