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

HRID 1092299Notes

Reaction equation

HRID 1092299 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[S:5][CH:6]=1.Cl.CN.[C:12]([BH3-])#[N:13].[Na+].[OH-].[Na+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:7][NH:13][CH3:12])[S:5][CH:6]=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 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.6 g of 4-bromothiophene-2-carbaldehyde are dissolved in 100 mL of acetonitrile, and 11.8 g of methylamine hydrochloride and 6.28 g of sodium cyanoborohydride are added. The reaction mixture is stirred overnight at room temperature. The reaction is stopped with 1 M sodium hydroxide solution. After evaporating off the solvents, the residue is chromatographed on silica gel (7/3 heptane/ethyl acetate). 8.19 g of (4-bromothiophen-2-ylmethyl)methylamine are obtained. Yield=79%.

Workup

  1. customAfter evaporating off the solvents
  2. customthe residue is chromatographed on silica gel (7/3 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-02c4de786aed4f4b9f1579f5f6c8fcd7
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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