Dimethylformamide → HCID 59398003, compound

HRID 39716Notes

Reaction equation

HRID 39716 reaction equation
CN(C)C=O.C(O)(=O)C.[OH:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH:15]1[C:20]([O:22][CH3:23])=[O:21].C(N(CC)CC)C.Br[CH2:32][CH2:33][S:34][C:35]1[S:36][CH:37]=[CH:38][CH:39]=1>C(OCC)(=O)C.O>[OH:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:32][CH2:33][S:34][C:35]2[S:36][CH:37]=[CH:38][CH:39]=2)[CH2:16][CH:15]1[C:20]([O:22][CH3:23])=[O:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 122011192-(2-Bromoethylthio)-thiopheneHCID 67539276HCID 67539276, compound

Product 1

HCID 59398003HCID 59398003, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To 3.1 mL of an N,N-dimethylformamide solution containing 0.12 g of methyl 4-(3-hydroxypropyl)piperidine-3-carboxylate acetate, 0.19 mL of triethylamine and 0.14 g of 2-((2-bromoethyl)thio)thiophene were added, and the mixture was stirred at 70 to 80° C. for 2.5 hours. Water and ethyl acetate were added thereto, and the organic layer was separated. The organic layer was washed sequentially with water and an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=50:1] to obtain 0.10 g of a brown oily substance, methyl 4-(3-hydroxypropyl)-1-(2-(2-thienylthio)ethyl)piperidine-3-carboxylate.

Workup

  1. additionwere added
  2. customthe organic layer was separated
  3. washThe organic layer was washed sequentially with water
  4. dry with materialan aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-ecb9a8ef7e0a4786bc75e2779c731656
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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