Disodium disulfite → HCID 117992247, compound

HRID 531057Notes

Reaction equation

HRID 531057 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[O:12]=[C:13]1[C:19]2[CH:20]=[CH:21][CH:22]=[N:23][C:18]=2[CH2:17][CH2:16][CH2:15][N:14]1[CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:26][CH2:25]1.S(OS([O-])=O)([O-])=O.[Na+].[Na+]>ClCCl>[O-:9][N+:23]1[C:18]2[CH2:17][CH2:16][CH2:15][N:14]([CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][CH2:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)=[O:31])[CH2:28][CH2:29]3)[C:13](=[O:12])[C:19]=2[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 24346Disodium disulfiteHCID 70297m-Chloroperbenzoic acidHCID 117992135HCID 117992135, compound

Product 1

HCID 117992247HCID 117992247, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (2.45 g) was added to a mixture of benzyl 4-(5-oxo-5,7,8,9-tetrahydro-6H-pyrido[3,2-c]azepin-6-yl)piperidine-1-carboxylate (1.8 g) and dichloromethane (50 mL), and the resultant mixture was stirred at room temperature for 3 hours. A 10% aqueous sodium disulfite solution was added to the reaction mixture, and the mixture was stirred for 20 minutes, followed by extraction with dichloromethane. The organic layer was washed with water and saturated saline and dried over sodium sulfate, and then, the solvent was distilled off under reduced pressure to obtain the title compound (1.0 g).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with water and saturated saline
  3. dry with materialdried over sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3960c1bd3d9a47669d1aa0646fca8c4a
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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