Ammonia → N-Methyl-3-(((2R)-1-methyl-2-pyrrolidinyl)methyl)-1H-indole-5-methanesulfonamide

HRID 651697Notes

Reaction equation

HRID 651697 reaction equation
[CH2:1]([N:8](C)[S:9]([CH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18](CC1C=CC=CC=1)[CH:17]=[C:16]2[CH2:29][C@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[CH3:35])(=[O:11])=[O:10])C1C=CC=CC=1.N.[Na].[Cl-].[NH4+]>O1CCCC1.O>[CH3:1][NH:8][S:9]([CH2:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]=[C:16]2[CH2:29][C@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[CH3:35])(=[O:10])=[O:11]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 53689728(r)-n-Benzyl-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1h-indol-5-yl]-n-methylmethanesulfonamide

Product 1

HCID 132552N-Methyl-3-(((2R)-1-methyl-2-pyrrolidinyl)methyl)-1H-indole-5-methanesulfonamideYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-N-Benzyl-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-N-methylmethanesulfonamide (from step (f), 2.04 g) in tetrahydrofuran (2 ml) was added dropwise to liquid ammonia (10 ml) at −40° C. under a nitrogen atmosphere. Sodium (approximately 500 mg) was then added portionwise to the colourless solution, until a permanent dark blue coloured solution was obtained. The blue solution was stirred for a further 30 min at −40° C. before saturated ammonium chloride solution (5 ml) was added and the grey slurry warmed to ambient temperature over an 8 hr period. The white slurry was then diluted with water (10 ml), filtered and dried in vacuo at 50° C. to give the title compound (733 mg, 56%) as a white solid. m.p. 209-213° C.

Workup

  1. customwas obtained
  2. additionwas added
  3. filtrationfiltered
  4. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-bc551b0675d8445a88ab1f733a50c2b4
Source dataset
uspto-grants-2001_08
Patent number
US06281357B1

Reaction notes

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