4-(N-Boc-amino)piperidine → {1-[2-(6-Cyano-quinolin-4-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

HRID 1782008Notes

Reaction equation

[CH:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[N:6]=[CH:5][CH:4]=1)=[CH2:2].[C:15]([O:19][C:20](=[O:28])[NH:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([CH3:18])([CH3:17])[CH3:16]>C(Cl)(Cl)Cl>[C:15]([O:19][C:20](=[O:28])[NH:21][CH:22]1[CH2:27][CH2:26][N:25]([CH2:2][CH2:1][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=3)[N:6]=[CH:5][CH:4]=2)[CH2:24][CH2:23]1)([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of (d) (150 mg, 0.8 mmol), piperidin-4-yl-carbamic acid tert-butyl ester (166 mg, 0.8 mmol) and chloroform (0.5 ml) were heated at 50° C. in a loosely capped vial for 6 hours. The product was purified by flash silica chromatography eluting with a 0-2% methanol in chloroform gradient affording the product as a foam (304 mg, 96%).

Workup

customThe product was purified by flash silica chromatography
washeluting with a 0-2% methanol in chloroform gradient

Sources & evidence

ORD record: ord-281727cb74e9404f8ec80ef3f0e73d68
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07498326B2

Reaction notes

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