Chloroacetyl chloride → HCID 86691443, compound

HRID 540329Notes

Reaction equation

[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][N:2]1[C:12]1[CH:21]=[C:20]([NH2:22])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.N12CCCN=C1CCCCC2.[Cl:34][CH2:35][C:36](Cl)=[O:37]>C(OCC)(=O)C>[Cl:34][CH2:35][C:36]([NH:22][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([N:2]2[CH2:3][CH2:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[CH2:1]2)[CH:21]=1)=[O:37]

Participants

Conditions

Temperature: 70 °C

Procedure

To the solution of 2-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)quinolin-4-amine (500 mg, 1.73 mmol) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.52 mL, 3.48 mmol) followed by chloroacetyl chloride (0.21 mL, 2.64 mmol) at room temperature. The resulting solution was heated with stirring at 70° C. for 2 hours under nitrogen. After cooled to room temperature, the reaction was diluted with ethyl acetate (50 mL), and then washed with water (50 mL×3). The organic phase was dried over sodium sulfate and concentrated under reduced pressure to give a residue which was purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:4) to give 140 mg of product as an off-white solid (yield was 22.1%). MS obsd. (ESI+) [(M+H)+] 366.

Workup

temperatureThe resulting solution was heated
temperatureAfter cooled to room temperature
washwashed with water (50 mL×3)
dry with materialThe organic phase was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customto give a residue which
customwas purified by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:4)

Sources & evidence

ORD record: ord-55f4e63b42c246589a7fb45484ad8fdb
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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