Acetic acid methanol → HCID 178476567, compound

HRID 2271531Notes

Reaction equation

HRID 2271531 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([NH:11]C(=O)OCC2C=CC=CC=2)[CH2:7][CH2:6]1)[CH3:3].CO.[C:24]([OH:27])(=[O:26])[CH3:25]>[Pd]>[C:24]([OH:27])(=[O:26])[CH3:25].[C:24]([OH:27])(=[O:26])[CH3:25].[CH3:3][N:2]([CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([NH2:11])[CH2:7][CH2:6]1)[CH3:1]

Participants

4

Reactant 2

HCID 10129899Acetic acid methanol2×HCID 66715796Carbamic acid, N-[trans-4-[(dimethylamino)methyl]cyclohexyl]-, phenylmethyl ester

Product 1

HCID 178476567HCID 178476567, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a flask containing Pd/C (1.5 g, Degussa type E101) was added methanol/acetic acid (100 mL, 3:1). Benzyl 4-((dimethylamino)methyl)cyclohexylcarbamate (15.8 g, 54 mmol) in methanol/acetic acid (300 mL, 3:1) was added. A balloon of H2 was added and the reaction stirred at rt for 6 h. The reaction was filtered through celite, the filtrate concentrated, and azeotroped with toluene. The thick oil was dried under vacuum to give desired product (17.9 g, crude) as a waxy solid. 1H NMR (300 MHz, MeOD) δ 3.11-2.98 (m, 1H), 2.78 (d, J=7.0 Hz, 2H), 2.69 (s, 6H), 2.07 (br d, J=13.9 Hz, 4H), 2.02-1.86 (m, 2H), 1.92 (s, 6H), 1.79-1.67 (m, 1H), 1.53-1.35 (m, 2H), 1.20-1.05 (m, 2H).

Workup

  1. additionA balloon of H2 was added
  2. filtrationThe reaction was filtered through celite
  3. concentrationthe filtrate concentrated
  4. customazeotroped with toluene
  5. customThe thick oil was dried under vacuum

Sources & evidence

ORD record
ord-da74a59c1e6d4ab8b0fba14c9ca384b4
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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