Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate → n-Tert-butoxycarbonyl-4-[4-(2h-tetrazol-5-yl)phenyl]piperazine

HRID 1356985Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Sn]([N:26]=[N+:27]=[N-:28])(C)C>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]3[N:26]=[N:27][NH:28][N:21]=3)=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 110 °C

Procedure

The intermediate 1A (6.0 g; 20.8 mmol) in solution in xylene (76 ml), under nitrogen, is treated with trimethyltin azide (6.25 g; 31.3 mmol). After stirring for 24 h at 110° C., the reaction medium is brought to room temperature and the precipitate formed is filtered on sintered glass and then washed with toluene and with petroleum ether. This solid is purified by chromatography on a silica gel column eluted with a dichloromethane/methanol/ammonium hydroxide mixture in the proportions 80/19/1 to give compound 1B (5.75 g; 87%) in the form of a white solid.

Workup

customis brought to room temperature
customthe precipitate formed
filtrationis filtered on sintered glass
washwashed with toluene and with petroleum ether
customThis solid is purified by chromatography on a silica gel column
washeluted with a dichloromethane/methanol/ammonium hydroxide mixture in the proportions 80/19/1

Sources & evidence

ORD record: ord-8bf43fedefcb41929f59655de86dfa4f
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589953B2

Reaction notes

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