2-Naphthalenesulfonyl chloride → HCID 86626635, compound

HRID 2424405Notes

Reaction equation

HRID 2424405 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].[CH3:15][CH:16]1[CH2:25][CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[N:26]2[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]2)[NH:17]1>N1C=CC=CC=1>[CH3:15][CH:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[N:26]2[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:30][CH2:31]2)[N:17]1[S:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 71252-Naphthalenesulfonyl chlorideHCID 57436182HCID 57436182, compound

Product 1

HCID 86626635HCID 86626635, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Naphthalenesulfonyl chloride (0.33 g, 1.45 mmol) was added to a solution of the tert-butyl 4-(1,2,3,4-tetrahydro-2-methylquinolin-5-yl)piperazine-1-carboxylate prepared in example 7 (0.4 g, 1.2 mmol), in pyridine (3 mL). The resulting mixture was heated under reflux for 3 h. The solvent was evaporated in vacuo and the residue was purified by column chromatography (using CH2Cl2 eluent). Yield: 0.26 g (41.2%). Rf=0.7 (CH2Cl2-acetone 98:2).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 h
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography (using CH2Cl2 eluent)

Sources & evidence

ORD record
ord-8645bbecac42487b8c0cb8cbde478d84
Source dataset
uspto-grants-2011_06
Patent number
US07964603B2

Reaction notes

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