Potassium Carbonate → HCID 20771335, compound

HRID 1814417Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.[C:11]1([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23]Br)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[C:11]1([NH:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][NH:10][CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 70 °C

Procedure

2(4-Chlorophenyl)ethylamine (1.8 g, 12 mmol) was added to a mixture of N-phenylcarbamoyl-3-bromopropylamine (2.5 g, 9.7 mmol) and potassium carbonate (2.6 g, 19 mmol) in CH3CN (50 ml). The mixture was stirred at 70° C. for 4.5 h, and then filtered. The filtrate was concentrated under vacuum to dryness, and the residue was dissolved with chloroform, washed with water, 1N-HCl and brine. The organic layer was dried over sodium sulfate, filtered, and then concentrated under vacuum to dryness. The residue was chromatographed on silica gel (eluting with 2% methanol/chloroform) to afford N-phenylcarbamoyl-N′-[2-(4- chlorophenyl)ethyl]-1,3- diaminopropane (1.43 g, 45%): MS(ES+) m/e 332 M+; 1H NMR (400 MHz, CD3OD) δ 7.35-7.15 (m, 8H), 6.99 (m, 1H), 3.31 (m, 2H), 3.23 (m, 2H), 3.06 (t, J=7.1 Hz, 2H), 3.00 (m, 2H), 1.89 (m, 2H).

Workup

filtrationfiltered
concentrationThe filtrate was concentrated under vacuum to dryness
dissolutionthe residue was dissolved with chloroform
washwashed with water, 1N-HCl and brine
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum to dryness
customThe residue was chromatographed on silica gel (eluting with 2% methanol/chloroform)

Sources & evidence

ORD record: ord-8fbbcf4aee1940528e58c8f626380a8f
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06875884B1

Reaction notes

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