Chloromethyl pivalate → 2-[(Diphenylmethylene)amino]-2-quinolin-4-ylethyl pivalate

HRID 1094643Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH2:12])=[CH:3][CH:2]=1.[C:13](=N)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:27]([O:33][CH2:34]Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:27]([O:33][CH2:34][CH:11]([N:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]

Participants

Conditions

Temperature: 50 °C

Procedure

A Stirred mixture of 1-quinolin-4-ylmethanamine (142 mg, 0.90 mmol, CHEMBRIDGE) and benzophenone imine (163 mg, 0.90 mmol) was heated at 50° C. for 2 hours. The resultant product was dissolved in dichloromethane (4 ml) and added to a solution of chloromethyl pivalate (136 mg, 0.90 mmol) and tetrabutylammonium bromide (150 mg, 0.465 mmol). 50% NaOHaq (0.9 ml) was added to the reaction mixture at 0° C. After the mixture was stirred at 0° C. for 1 hour, the reaction was diluted with dichloromethane (30 ml) and water (30 ml). The organic layer was separated, dried over Na2SO4, concentrated in vacuo and purified through silica gel column chromatography eluting with Hexane/EtOAc (3:1 to 2:1) to furnish the title compound (142 mg, 36% yield) as colorless oil. MS (ESI) m/z 437 (M+H)+.

Workup

addition50% NaOHaq (0.9 ml) was added to the reaction mixture at 0° C
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
custompurified through silica gel column chromatography
washeluting with Hexane/EtOAc (3:1 to 2:1)

Sources & evidence

ORD record: ord-6a8ad00a50aa41f0b50b967fa1201461
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08134004B2

Reaction notes

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