N-Methylbenzylamine → Methyl 5-((benzyl(methyl)amino)methyl)-3-phenylthiophene-2-carboxylate

HRID 1186716Notes

Reaction equation

HRID 1186716 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1)=O.[CH3:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH2:20]([N:19]([CH2:1][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1)[CH3:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 7669N-MethylbenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 71742493Methyl 5-formyl-3-phenylthiophene-2-carboxylate

Product 1

HCID 58121139Methyl 5-((benzyl(methyl)amino)methyl)-3-phenylthiophene-2-carboxylateYield 94.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 172 (0.706 g, 2.87 mmol) in DCE (15 mL) was added N-Methylbenzylamine (0.388 mL, 3.01 mmol) and sodium triacetoxyborohydride (0.851 g, 4.01 mmol) and stirred for 18 hours. The reaction mixture was diluted in DCM and washed with a saturated solution of sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and evaporated. The crude residue was purified by ISCO (40 g column, 0-30% ethyl acetate in hexanes) to yield compound 173 (951 mg, 94%) a colorless oil.

Workup

  1. washwashed with a saturated solution of sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude residue was purified by ISCO (40 g column, 0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0c58cd2c011e411981726d19e7b0249a
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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