Methanesulfonyl chloride → HCID 23001031, compound

HRID 397706Notes

Reaction equation

HRID 397706 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[NH3:1].[CH2:14]([N:11]1[CH2:12][CH2:13][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[CH:3]=2)[CH2:9][CH2:10]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 23000985HCID 23000985, compound

Product 2

HCID 222AmmoniaHCID 23001031HCID 23001031, compoundYield 130.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(3-aminophenyl)-N-hexylpiperidine (Preparation 50, 178 mg, 0.68 mmol) in pyridine (5 ml) at room temperature under an atmosphere of nitrogen was added methanesulfonyl chloride (79 ml, 1.03 mmol) over 10 min. The resultant mixture was stirred overnight, poured onto water (10 ml) and extracted with ethyl acetate (3×10 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo at 80° C. to give the crude product which was purified by silica column chromatography, eluting with ethyl acetate:hexane:0.880 ammonia (90:9:1) to give the title compound as a pale brown oil (150 mg, 65%).

Workup

  1. additionpoured onto water (10 ml)
  2. extractionextracted with ethyl acetate (3×10 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo at 80° C.
  5. customto give the crude product which
  6. customwas purified by silica column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-c74909ffbc4646608e0422ed6cbddb69
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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