4-(Benzyloxy)phenyl isocyanate → 4-[4-(4-Benzyloxyphenylaminocarbonyl)piperazin-1-yl]-7-chloroquinoline

HRID 1353367Notes

Reaction equation

HRID 1353367 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCCCCC.CCOC(C)=O>C1COCC1>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([N:15]2[CH2:16][CH2:17][N:12]([C:6]3[C:5]4[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:9]=[CH:8][CH:7]=3)[CH2:13][CH2:14]2)=[O:34])=[CH:28][CH:27]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 2562684-(Benzyloxy)phenyl isocyanateHCID 7383897-Chloro-4-(piperazin-1-yl)quinolineHCID 21226206Ethyl acetate hexane

Product 1

HCID 211016894-[4-(4-Benzyloxyphenylaminocarbonyl)piperazin-1-yl]-7-chloroquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-Chloro-4-(piperazin-1-yl)quinoline (62 mg, 0.25 mmol) and 4-benzyloxyphenyl isocyanate (68 mg, 0.30 mmol) in THF (10 mL) are reacted according to method C yielding the title product as a yellow solid after column chromatography with hexane-EtOAc.

Sources & evidence

ORD record
ord-577c554a8e9242efbe850bd89c978717
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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