N-Methylsulfamoyl chloride → HCID 19992426, compound

HRID 345434Notes

Reaction equation

HRID 345434 reaction equation
[CH3:1][NH:2][S:3](Cl)(=[O:5])=[O:4].[NH2:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1>N1C=CC=CC=1>[CH3:1][NH:2][S:3]([NH:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[CH2:18][CH2:19]2)=[CH:10][CH:9]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 11789235N-Methylsulfamoyl chloride2×HCID 19992424HCID 19992424, compound

Product 1

HCID 19992426HCID 19992426, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methylsulphamoyl chloride (0.39 g) was added dropwise to a stirred solution of 4-[(4-aminophenoxy)methyl]-1-[4-pyridyl]-piperidine (see Preparation 4) (0.57 g) in pyridine (15 ml) and the mixture was stirred at room temperature for 6 hours. An additional 0.39 g of methylsulphamoyl chloride was then added and the mixture was stirred for a further 18 hours and then evaporated. The residue was partitioned between sodium bicarbonate solution and ethyl acetate. The organic layer was separated and the aqueous layer was extracted several times with ethyl acetate. The combined organic layers were washed with water, dried (Na2SO4) and evaporated. The solid residue was crystallised from ethanol to give the title compound, (0.30 g), m.p. 170.5°-172.5°.

Workup

  1. stirringthe mixture was stirred for a further 18 hours
  2. customevaporated
  3. customThe residue was partitioned between sodium bicarbonate solution and ethyl acetate
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted several times with ethyl acetate
  6. washThe combined organic layers were washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe solid residue was crystallised from ethanol

Sources & evidence

ORD record
ord-4dcc3d9b79ea4841b42825ae199dd4ca
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

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