Dichloromethane → Ammonia

HRID 428892Notes

Reaction equation

HRID 428892 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH2:20])[CH3:13])[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:21][S:22](Cl)(=[O:24])=[O:23].ClCCl>N1C=CC=CC=1>[NH3:7].[CH2:1]([N:7]1[CH2:8][CH:9]2[CH:11]([C:10]2([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[NH:20][S:22]([CH3:21])(=[O:24])=[O:23])[CH3:13])[CH2:12]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 22141160HCID 22141160, compound

Product 2

HCID 222AmmoniaHCID 22141179HCID 22141179, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-[3-hexyl-6-methyl-3-azabicyclo[3.1.0]hex-6-yl]phenylamine (Preparation 140, 30 mg, 0.11 mol) in pyridine (1.0 ml) under a nitrogen atmosphere at room temperature was added dropwise methane sulfonyl chloride (13 μl, 0.16 mmol), and the reaction mixture was stirred at room temperature for 2 d. Ice (2 g) and dichloromethane (5 ml) were added, the layers were separated and the aqueous layer was further extracted with dichloromethane (5 ml). The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo. This was purified by chromatography using silica gel (1.5 g) eluting with dichloromethane:ethanol:0.880 ammonia (200:8:1) to afford the title compound as a very pale yellow oil (5.2 mg, 14%).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was further extracted with dichloromethane (5 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis was purified by chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6e11d1f6791f4b4bb1a4307dcf1d0265
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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