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

HRID 258712Notes

Reaction equation

HRID 258712 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 recrystallised 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-1c0fc56b21124a86b1764bb51ba8f5f9
Source dataset
uspto-grants-1977_07
Patent number
US04034098

Reaction notes

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