Dichloromethane → HCID 23001045, compound

HRID 397713Notes

Reaction equation

HRID 397713 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:20][CH2:21][CH3:22])[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.[CH2:23]([S:25](Cl)(=[O:27])=[O:26])[CH3:24].ClCCl>N1C=CC=CC=1>[NH3:1].[CH2:23]([S:25]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:20][CH2:21][CH3:22])[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)(=[O:27])=[O:26])[CH3:24]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 11667Ethanesulfonyl chlorideHCID 23000976HCID 23000976, compound

Product 2

HCID 222AmmoniaHCID 23001045HCID 23001045, compoundYield 119.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-(3-aminophenyl)-N-hexyl-4-n-propylpiperidine (Preparation 70, 34 mg, 0.11 mmol) in pyridine (0.5 ml) under nitrogen was added ethanesulfonyl chloride (16 ml, 0.17 mmol) and the resultant mixture was stirred overnight. Ice (2 g) was added and, after 15 min, dichloromethane (3 ml) was added and the biphasic mixture was left to stir for 15 min. The layers were separated and the aqueous layer was extracted with dichloromethane (3 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by silica (5 g) column chromatography eluting with ethyl acetate:hexane:0.880 ammonia (40:60:1 to 75:25:1) to give the title compound as a pale yellow oil (26 mg, 60%).

Workup

  1. waitthe biphasic mixture was left
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with dichloromethane (3 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give the crude product
  7. customThis was purified by silica (5 g) column chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-98efeb575e3b4331af759f17f7aa7916
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

Loading…