Oxalyl chloride → tert-Butyl 4-(4-chlorocarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

HRID 1712513Notes

Reaction equation

HRID 1712513 reaction equation
C(Cl)(=O)C([Cl:4])=O.[C:7]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]2[O:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]3[O:39][CH2:38][C:37](=[O:40])[N:36]([CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:35]=3[CH:46]=2)=[CH:12][CH:11]=1)(O)=[O:8]>ClCCl.CN(C)C=O>[Cl:4][C:7]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH:17]2[O:29][CH2:30][C:31]2[CH:32]=[CH:33][C:34]3[O:39][CH2:38][C:37](=[O:40])[N:36]([CH2:41][CH2:42][CH2:43][O:44][CH3:45])[C:35]=3[CH:46]=2)=[CH:12][CH:11]=1)=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 68499317tert-butyl 4-(4-carboxyphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Product 1

HCID 86610013tert-Butyl 4-(4-chlorocarbonylphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

0.190 ml of oxalyl chloride are added dropwise to a solution of 0.600 g of tert-butyl 4-(4-carboxyphenyl)-3-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]piperidine-1-carboxylate in 6 ml of dichloromethane. The reaction solution is subsequently stirred at room temperature over 1 hour and then admixed with 2 drops of N,N-dimethylformamide and stirred at room temperature for a further 35 minutes. The reaction mixture is concentrated by evaporation to dryness and used further as the crude product without purification. Reddish oil, Rt=5.50.

Workup

  1. stirringstirred at room temperature for a further 35 minutes
  2. concentrationThe reaction mixture is concentrated by evaporation to dryness
  3. customused further as the crude product without purification

Sources & evidence

ORD record
ord-2c687e30c61d48e6a07fca777c1be159
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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