Triethylamine → HCID 86659059, compound

HRID 2407744Notes

Reaction equation

HRID 2407744 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[S:26][C:25]([S:27](Cl)(=[O:29])=[O:28])=[CH:24][CH:23]=1.C(N(CC)CC)C>ClCCl>[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[S:26][C:25]([S:27]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3][CH2:2]2)(=[O:29])=[O:28])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chloride

Product 1

HCID 86659059HCID 86659059, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl piperidin-4-ylmethylcarbamate (0.100 g) in dichloromethane (2.3 mL) was treated with 5-(pyridin-2-yl)thiophene-2-sulfonyl chloride (0.133 g), followed by triethylamine (0.325 mL) at room temperature. After stirring the mixture at room temperature overnight, it was washed with 1N hydrochloric acid, the organic layer was separated and filtered. Evaporation of the solvent and purification by column chromatography on silica gel (1-4% methanol in dichloromethane) provide the title compound (0.088 g) having the following physical data.

Workup

  1. washwas washed with 1N hydrochloric acid
  2. customthe organic layer was separated
  3. filtrationfiltered
  4. customEvaporation of the solvent and purification by column chromatography on silica gel (1-4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0220c6c7373d40379df6e5fad5a2e003
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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