Bis(2-chloroethyl)amine hydrochloride → 2-Chloro-5-Piperazin-1-yl-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2298042Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8].Cl.Cl[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]Cl>C1(C)C(C)=CC=CC=1>[Cl:22][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]3)[CH2:20]1)[CH2:18]2)=[O:8]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 5-amino-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (1.00 g, Example 4b) in xylene (20 ml) was added bis-(2-chloroethyl)amine hydrochloride salt (0.620 g). The mixture was heated at 150° C. for 12 h (a dark solution is obtained). The cold solution was washed with 2M HCl, the aqueous layer washed with ethyl acetate then basified with sodium bicarbonate and extracted twice with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to give a foam. The crude material was purified on silica gel (0-10% ethanol/dichloromethane), to afford the title compound as a white solid (0.90 g).

Workup

customis obtained)
washThe cold solution was washed with 2M HCl
washthe aqueous layer washed with ethyl acetate
extractionextracted twice with dichloromethane
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationthe filtrate concentrated under reduced pressure
customto give a foam
customThe crude material was purified on silica gel (0-10% ethanol/dichloromethane)

Sources & evidence

ORD record: ord-3fdcfd9aef704c199099ddbd24bd4556
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492355B1

Reaction notes

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