Hydrochloric Acid → 2-(2-Morpholinyl)-4,5,6,7-tetrahydro-1H-benzimidazole

HRID 2367344Notes

Reaction equation

HRID 2367344 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[NH:18][C:17]4[CH2:19][CH2:20][CH2:21][CH2:22][C:16]=4[N:15]=3)[CH2:9]2)C=CC=CC=1.Cl>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[NH:15][C:16]3[CH2:22][CH2:21][CH2:20][CH2:19][C:17]=3[N:18]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 585048062-[4-(Phenylmethyl)-2-morpholinyl]-4,5,6,7-tetrahydro-1H-benzimidazole

Product 1

HCID 585044142-(2-Morpholinyl)-4,5,6,7-tetrahydro-1H-benzimidazoleYield 147.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-[4-(Phenylmethyl)-2-morpholinyl]-4,5,6,7-tetrahydro-1H-benzimidazole (0.78 g, 2.62 mmol) was hydrogenated in ethanol (30 mL) in the presence of Pd/C (10 wt %, 0.279 g, 0.262 mmol). To the reaction mixture was added 0.2 mL of concentrated hydrochloric acid. After stirring at room temperature overnight, the catalyst was filtered off. The filtrate was concentrated to afford the title compound (0.8 g) as a yellow oil. LC-MS (ES) m/z=208 [M+H]+.

Workup

  1. filtrationthe catalyst was filtered off
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-49179edbbc5e499aaebf2cf1e331f81e
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…