Methylamine → 1-(Benzofuran-3-ylacetyl)-n-methyl-4-piperidinecarboxamide

HRID 430602Notes

Reaction equation

HRID 430602 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([CH2:22][C:23]([N:25]2[CH2:30][CH2:29][CH:28]([C:31]([OH:33])=O)[CH2:27][CH2:26]2)=[O:24])=[CH:14]1.CN>ClCCl.O>[O:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([CH2:22][C:23]([N:25]2[CH2:30][CH2:29][CH:28]([C:31]([NH:3][CH3:1])=[O:33])[CH2:27][CH2:26]2)=[O:24])=[CH:14]1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 155123841-(Benzofuran-3-ylacetyl)-4-piperidinecarboxlic acid

Product 1

HCID 155123851-(Benzofuran-3-ylacetyl)-n-methyl-4-piperidinecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

19 g of carbonyldiimidazole are added in portions to 33 g of the product obtained in Step B in 350 ml of dichloromethane. When the evolution of gas has stopped, the reaction mixture is stirred for 1 hour at room temperature and then a stream of methylamine is circulated through it. After 12 hours' stirring, the mixture is diluted with water, decanted, washed with 1N sodium hydroxide solution and then with 1N hydrochloric acid, decanted, dried and evaporated, enabling the expected product to be isolated.

Workup

  1. stirringAfter 12 hours' stirring
  2. customdecanted
  3. washwashed with 1N sodium hydroxide solution
  4. customwith 1N hydrochloric acid, decanted
  5. customdried
  6. customevaporated
  7. customto be isolated

Sources & evidence

ORD record
ord-0b9e071e1d9f42e5921596c792080760
Source dataset
uspto-grants-2001_11
Patent number
US06323217B2

Reaction notes

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