Triethylamine → N-[(Piperidin-4-yl)methyl]isoquinoline-5-sulfonamide

HRID 1722614Notes

Reaction equation

HRID 1722614 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[CH:16]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[C:20]=2[CH:19]=[CH:18][N:17]=1>ClCCl>[NH:6]1[CH2:7][CH2:8][CH:3]([CH2:2][NH:1][S:26]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]3[C:20]=2[CH:19]=[CH:18][N:17]=[CH:16]3)(=[O:27])=[O:28])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 235274-(Aminomethyl)piperidineHCID 33716555-Isoquinolinesulfonyl chloride

Product 1

HCID 14623234N-[(Piperidin-4-yl)methyl]isoquinoline-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dissolve 5.02 g of 4-aminomethylpiperidine and 22 g of triethylamine in 50 ml of dichloromethane. Add dropwise over 30 minutes 5.0 g of 5-isoquinoline sulfonyl chloride dissolved in 50 ml of dichloromethane while cooling the mixture in an ice bath. Stir at room temperature for 72 hours. Filter the reaction mixture and evaporate the filtrate. Chromatograph the residue over 400g of silica gel eluting with dichloromethane/methanol (9/1). Obtain the title compound by evaporating the appropriate fractions, as determined by thin layer chromatography. Dissolve the product in ethanol saturated with HCl and evaporate to obtain the title compound as the dihydrochloride salt. FAB MS (M+1)e =306.

Workup

  1. temperaturewhile cooling the mixture in an ice bath
  2. filtrationFilter the reaction mixture
  3. customevaporate the filtrate

Sources & evidence

ORD record
ord-37c227ca22af461591368902b4fe82f4
Source dataset
uspto-grants-1989_08
Patent number
US04857301

Reaction notes

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