Water → 2-[4-(Phenylmethyl)-2-morpholinyl]-4,5,6,7-tetrahydro-1H-benzimidazole

HRID 2367343Notes

Reaction equation

HRID 2367343 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]([CH:11]1[O:16][CH2:15][CH2:14][N:13]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:12]1)=O.FC(F)(F)C([O-])=O.[NH4+:31].O>C(Cl)Cl>[C:18]1([CH2:17][N:13]2[CH2:14][CH2:15][O:16][CH:11]([C:9]3[NH:8][C:3]4[CH2:4][CH2:5][CH2:6][CH2:7][C:2]=4[N:31]=3)[CH2:12]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724268Ammonium trifluoroacetateHCID 58504386N-[(1R)-2-Oxocyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide

Product 1

HCID 585048062-[4-(Phenylmethyl)-2-morpholinyl]-4,5,6,7-tetrahydro-1H-benzimidazoleYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of N-[(1R)-2-oxocyclohexyl]-4-(phenylmethyl)-2-morpholinecarboxamide (1.1 g, 3.48 mmol) and ammonium trifluoroacetate (2.069 g, 17.38 mmol) was heated at 150° C. for 20 minutes. After cooling, to the mixture was added water (30 mL) and CH2Cl2 (50 mL). The organic layer was separated and washed with brine, dried (MgSO4), and concentrated to afford the crude title compound (0.78 g). LC-MS (ES) m/z=298 [M+H]+.

Workup

  1. temperatureAfter cooling, to the mixture
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-beec93d0d9484cfd8a74eb0fcc4060c8
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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