Triethylamine → 1-(4-Bromothiophen-2-yl)-N-methylmethanamine

HRID 910314Notes

Reaction equation

HRID 910314 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[Br:5][C:6]1[CH:7]=[C:8]([CH:11]=O)[S:9][CH:10]=1.Cl.CN.C(N(CC)CC)C>C(OCC)(=O)C.O>[Br:5][C:6]1[CH:7]=[C:8]([CH2:11][NH:2][CH3:1])[S:9][CH:10]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 877924-Bromothiophene-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 422820341-(4-Bromothiophen-2-yl)-N-methylmethanamineYield 53.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

25.2 g (360 mmol) of sodium cyanoborohydride are added to a solution of 35 g (180 mmol) of 4-bromothiophene-2-carbaldehyde, 62 g (640 mmol) of methylamine hydrochloride and 119 ml (846 mmol) of triethylamine. The reaction medium is stirred at room temperature for 3.5 hours. After addition of water and ethyl acetate and washing with aqueous 1M sodium hydroxide solution, the organic phase is extracted. The ethyl acetate phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with a 90/10 to 70/30 heptane/ethyl acetate mixture. 19.7 g (52%) of (4-bromothiophen-2-ylmethyl)methylamine are obtained.

Workup

  1. washwashing with aqueous 1M sodium hydroxide solution
  2. extractionthe organic phase is extracted
  3. dry with materialThe ethyl acetate phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by thin-layer chromatography on silica
  8. washeluted with a 90/10 to 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-856cda6114524a4c8cc92bb1deef60d0
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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