Benzyl Alcohol → 1-(Pyridin-4-yl)piperidine-4-carbamic acid benzyl ester

HRID 412622Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10](C(O)=O)[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.C([N:18]([CH2:21]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>CN(C)C=O>[CH2:40]([O:47][C:21](=[O:30])[NH:18][CH:10]1[CH2:9][CH2:8][N:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:12][CH2:11]1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 1-(pyridin-4-yl)piperidine-4-carboxylic acid (11.18 g) and triethylamine (11.3 ml) in dimethylformamide (110 ml) was added diphenylphosphoryl azide (12.9 ml) at room temperature, and the mixture was stirred at 80° C. for 30 min. Benzyl alcohol (6.17 ml) was added at the same temperature, and the mixture was stirred for 12 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=99:1-95:5) and dried under reduced pressure to give the title compound (9.46 g).

Workup

stirringthe mixture was stirred for 12 hours
customAfter completion of the reaction
customthe solvent was evaporated
customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=99:1-95:5)
customdried under reduced pressure

Sources & evidence

ORD record: ord-82a0b3d961e04a4680847d4b53b7ebcd
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562828B1

Reaction notes

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