Pyridine → (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]methanesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][CH:8]([NH2:11])[CH2:9][CH3:10].N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl.C(OCC)C>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C@H:8]([NH:11][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:9][CH3:10]Participants
Procedure
Five grams of 3-chloro-2-(2-aminobutyl)thiophene is dissolved in 10 ml of methylene chloride in a 3-neck round bottomed flask blanketed with an inert atmosphere at 0° C. Pyridine (2.2 ml) is added in one portion followed by 2.05 ml of methanesulfonyl chloride. After warming to room temperature, the mixture is stirred for 4 hours before diluting with 100 ml of diethyl ether. The solution is poured into a separatory funnel and washed with water, dilute 2N HCl, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]methanesulfonamide (5.5 g) as an orange oil which solidifies upon standing in a refrigerator overnight. MS: m/z (EI, 70EV) 267 (5%). 1H NMR (200 MHz; CDCl3): δ 1.0 (3H, t, CH3), 1.6 (2H, m, CH2), 2.65 (3H, s, CH3), 3.0 (2H, m, CH2), 3.6 (1H, m, CH), 6.9 (1H, d, CH), 7.2 (1H, d, CH).
Workup
- customblanketed with an inert atmosphere at 0° C
- additionThe solution is poured into a separatory funnel
- washwashed with water
- additiondilute 2N HCl, saturated aqueous sodium bicarbonate and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-deac3d0398e142e982ad3fabb730e59d
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06429315B1
Reaction notes
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