Sodium Hydroxide → 1-(4-Bromothiophen-2-yl)-N-methylmethanamine

HRID 910275Notes

Reaction equation

HRID 910275 reaction equation
Cl.CN.[C:4]([BH3-])#[N:5].[Na+].[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=O)[S:12][CH:13]=1.[OH-].[Na+]>CO>[Br:8][C:9]1[CH:10]=[C:11]([CH2:14][NH:5][CH3:4])[S:12][CH:13]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 877924-Bromothiophene-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 422820341-(4-Bromothiophen-2-yl)-N-methylmethanamineYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

18 g (260 mmol) of methylamine hydrochloride and then 7.5 g (100 mmol) of sodium cyanoborohydride are successively added to a solution of 10 g (50 mmol) of 4-bromo-2-thiophenecarboxaldehyde in 150 ml of methanol. The reaction medium is stirred at room temperature for 24 hours and then filtered under vacuum. After evaporating the filtrate to dryness, the residue is taken up in dichloromethane. The organic phase obtained is washed with 1N hydrochloric acid solution. The aqueous phase thus obtained is treated with aqueous 1N sodium hydroxide solution and extracted with dichloromethane. The organic phase is dried over magnesium sulfate, filtered and evaporated under vacuum. 4.5 g (44%) of (4-bromothiophen-2-ylmethyl)methylamine are obtained.

Workup

  1. filtrationfiltered under vacuum
  2. customAfter evaporating the filtrate to dryness
  3. customThe organic phase obtained
  4. washis washed with 1N hydrochloric acid solution
  5. customThe aqueous phase thus obtained
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-6c3630afe13c4c50aaf0eae8260f8850
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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