5-Bromothiophene-2-carbaldehyde → N-[(5-bromothien-2-yl)methyl]-N-methylamine

HRID 910289Notes

Reaction equation

HRID 910289 reaction equation
Cl.CN.[Br:4][C:5]1[S:9][C:8]([CH:10]=O)=[CH:7][CH:6]=1.[C:12]([BH3-])#[N:13].[Na+].CCCCCCC.ClCCl>C(O)C.CO.C(OCC)(=O)C>[Br:4][C:5]1[S:9][C:8]([CH2:10][NH:13][CH3:12])=[CH:7][CH:6]=1

Participants

8

Reactant 4

HCID 784285-Bromothiophene-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 21907733Dichloromethane heptane

Product 1

HCID 2449439N-[(5-bromothien-2-yl)methyl]-N-methylamineYield 77.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

14 g (209 mmol) of methylamine hydrochloride are added to a solution of 5 g (42 mmol) of 5-bromothiophene-2-carboxaldehyde in 80 ml of ethanol and 40 ml of methanol. The reaction medium is cooled to 0° C. and 5.8 g (83.8 mmol) of sodium cyanoborohydride are added. The reaction medium is stirred at 0° C. for 5 hours, hydrolysed and diluted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated. The residue obtained is taken up in a 70/30 heptane/dichloromethane mixture and then filtered. 6.7 g of crude residue are obtained.

Workup

  1. washThe organic phase is washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c137ebadaa324fec98d46e60ee42be54
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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