Methylamine → N-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methylene)-methanamine

HRID 475193Notes

Reaction equation

HRID 475193 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]=O)=[CH:15][C:10]=2[N:9]=[CH:8]1.[CH3:18][NH2:19]>CO.CCO>[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:19][CH3:18])=[CH:15][C:10]=2[N:9]=[CH:8]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 866947231-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carbaldehyde

Product 1

HCID 71272746N-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methylene)-methanamineYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 64 (1.0 g, 4.34 mmol) in MeOH (10 mL) at 0° C. was added a solution of MeNH2 in EtOH (33%, 2 mL). After stirring at RT for 2 h, the mixture was concentrated under reduced pressure to afford 1.0 g (94%) of N-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methylene)-methanamine (66) as yellow oil: MS (ESI) m/z=244.2 [M+1]+.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a0581432be9a46a89d5e6ea4ce6953f3
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

Loading…