1,4-Dioxane hydrochloride → 1-(4-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)-N-methylmethanamine

HRID 475262Notes

Reaction equation

HRID 475262 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:17][N:18](C)[C:19](=O)OC(C)(C)C.Cl.O1CCOCC1>CO>[Cl:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:17][NH:18][CH3:19]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86694745tert-butyl (4-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl(methyl)carbamate

Product 1

HCID 712721921-(4-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)-N-methylmethanamineYield 146,700.406%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 218 (363 mg, 0.96 mmol) in MeOH (6 mL) was added 4N HCl/dioxane (2.87 ml, 11.5 mmol) and the reaction was stirred at RT for 2 h then concentrated in vacuo to afford 394 g (100%) of 1-(4-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)-N-methylmethanamine (220) as its bis-HCl salt: MS (ESI) m/z=280.1 [M+1]+.

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-93269cb71c8a445fb2a4d7a3c96206de
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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