Triethylamine → N-{1-[2-(1H-Indol-3-yl)ethyl]piperidin-4-yl}methanesulfonamide

HRID 66302

Reaction equation

HRID 66302 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[NH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:9][CH2:8][N:5]2[CH2:6][CH2:7][CH:2]([NH:1][S:27]([CH3:26])(=[O:29])=[O:28])[CH2:3][CH2:4]2)=[CH:11]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2154154-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrate

Product 1

HCID 22754838N-{1-[2-(1H-Indol-3-yl)ethyl]piperidin-4-yl}methanesulfonamideYield 105.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-[2-(4-Amino-1-piperidyl)ethyl]indole (1.307 g.) suspended in a solution of triethylamine (2 mls.) in dichloromethane (10 mls.) at room temperature with stirring was added methane sulphonyl chloride (0.570 g.) in dichloromethane (5 mls.). After stirring for 18 hours the solution was washed with water and the organic phase separated, dried and evaporated to yield the title compound (1.690 g.) as an oil. This was recrystallized from ethanolic hydrogen chloride as the hydrochloride salt (0.560 g., m.p. 241°-242° C.).

Workup

  1. stirringAfter stirring for 18 hours the solution
  2. washwas washed with water
  3. customthe organic phase separated
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-945371300be648fc962154efaeb99079
Source dataset
uspto-grants-1978_12
Patent number
US04131680

Linked notes

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