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

HRID 1894836Notes

Reaction equation

HRID 1894836 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 1M 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-63fe312434bb4771a562af49949cc940
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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