Methanesulfonyl chloride → N-[4-([1-(Benzyloxycarbonyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamide

HRID 345447Notes

Reaction equation

HRID 345447 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:30]=[CH:29][C:10]([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[CH2:22]([O:21][C:19]([N:16]1[CH2:15][CH2:14][CH:13]([CH2:12][O:11][C:10]2[CH:29]=[CH:30][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=2)[CH2:18][CH2:17]1)=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 199924324-[(4-Aminophenoxy)methyl]-1-(benzyloxycarbonyl)piperidine

Product 1

HCID 19992429N-[4-([1-(Benzyloxycarbonyl)piperidin-4-yl]methoxy)phenyl]methanesulphonamideYield 81.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl chloride (1.91 g) was added to a stirred solution of the product of part (iii) (5.15 g) in pyridine (50 ml) at 0°. The solution was stirred at room temperature for 18 hours and then evaporated. The residue was treated with aqueous sodium bicarbonate solution and the mixture was extracted several times with ethyl acetate. The combined extracts were washed with water, dried (Na2SO4) and evaporated. The residue was crystallised from ethyl acetate/hexane to give the title compound, (5.17 g), m.p. 150°-151°.

Workup

  1. customevaporated
  2. additionThe residue was treated with aqueous sodium bicarbonate solution
  3. extractionthe mixture was extracted several times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-df94d09ffb7743f89e27dbd011e13789
Source dataset
uspto-grants-1991_10
Patent number
US05057528

Reaction notes

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