Sodium borohydride → N-methyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamine

HRID 475194Notes

Reaction equation

HRID 475194 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH:16]=[N:17][CH3:18])=[CH:15][C:10]=2[N:9]=[CH:8]1.[BH4-].[Na+]>CO>[CH3:18][NH:17][CH2:16][C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)[CH:8]=[N:9][C:10]=2[CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 71272746N-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methylene)-methanamine

Product 1

HCID 71272704N-methyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamineYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 66 (1.0 g, 4.11 mmol) in MeOH (10 mL) cooled to 0° C. was added NaBH4 (300 mg, 8.23 mmol). After stirring at RT overnight, the mixture was quenched with water (3 mL) and extracted with DCM (3×50 mL). The organic layers were separated, washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford 880 mg (66%) of N-methyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamine (68) as yellow oil: MS (ESI) m/z=246.2 [M+1]+.

Workup

  1. customthe mixture was quenched with water (3 mL)
  2. extractionextracted with DCM (3×50 mL)
  3. customThe organic layers were separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e18b0fc045e4e019bb0f7b378fe17e6
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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