2-Thiophenecarboxaldehyde → HCID 14026221, compound

HRID 2267473Notes

Reaction equation

HRID 2267473 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl.C(=O)(O)[O-].[Na+]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

7

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 14026221HCID 14026221, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2-Thiophenecarboxaldehyde (1 g, 8.9 mmol) was dissolved in dichloroethane and treated with piperidine and sodium triacetoxyborohydride. The reaction was stirred at room temperature overnight. The reaction was diluted with dichloromethane and aqueous saturated sodium bicarbonate. The organic layer was separated out, washed with water and brine and dried with sodium sulfate. The volatile were removed in vacuo and the residue was purified by column chromatography on silica gel using a gradient of 2 to 8% of methanol in dichloromethane to obtain a brown oil. Yield=1.5 g. MS (M+H)+ 182.

Workup

  1. customThe organic layer was separated out
  2. washwashed with water and brine
  3. dry with materialdried with sodium sulfate
  4. customThe volatile were removed in vacuo
  5. customthe residue was purified by column chromatography on silica gel using a gradient of 2 to 8% of methanol in dichloromethane
  6. customto obtain a brown oil

Sources & evidence

ORD record
ord-82391d9c14f748ea82522ad0db861645
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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