Pyridine → HCID 69100863, compound

HRID 2115102Notes

Reaction equation

HRID 2115102 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:26])[CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[CH:7]=[CH:8][CH:9]=1.N1C=CC=CC=1.[Cl:33]CCl.[CH3:36][S:37]([Cl:40])(=[O:39])=[O:38]>C(=O)([O-])O.[Na+]>[ClH:33].[ClH:40].[CH2:19]([CH:16]1[CH2:17][CH2:18][N:13]([CH2:12][C:11]([NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([NH:3][S:37]([CH3:36])(=[O:39])=[O:38])[CH:5]=2)=[O:26])[CH2:14][CH2:15]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 69099963HCID 69099963, compound

Product 1

HCID 69100863HCID 69100863, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 0.36 g (1 mmol) of N-(3-amino-phenyl)-2-(4-benzyl-piperidin-1-yl)-acetamide dihydrochloride (Example 175) and 0.24 ml (3 mmol) of pyridine in 10 ml of dichloromethane 0.16 ml (2 mmol) of methanesulfonyl chloride in 5 ml of dichloromethene is added dropwise below 10° C., and the reaction mixture is stirred at room temperature for 10 hours. Then 20 ml of 8% sodium hydrogencarbonate solution is added to the mixture, the organic layer is separated and the water phase is extracted three times with 10 ml of dichloromethane. The combined organic layers are washed with 20 ml of water and dried over sodium sulfate, concentrated, the residue is treated with diethylether and 2.5 N hydrochloric acid in ethyl acetate and the precipitated crystals are filtered off to yield 0.32 g (73%) of the title compound. Melting Point: 110-114° C. (diethylether-ethyl acetate)

Workup

  1. customthe organic layer is separated
  2. extractionthe water phase is extracted three times with 10 ml of dichloromethane
  3. washThe combined organic layers are washed with 20 ml of water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. additionthe residue is treated with diethylether and 2.5 N hydrochloric acid in ethyl acetate
  7. filtrationthe precipitated crystals are filtered off

Sources & evidence

ORD record
ord-67e03d5eed424adaa92d3616a8f09ece
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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