Ethanol → 1-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine

HRID 1687470Notes

Reaction equation

HRID 1687470 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][C:4]=1[N+:20]([O-])=O.C(O)C.[H][H]>[Pd]>[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:12][CH2:13][C:7]=2[CH:6]=[CH:5][C:4]=1[NH2:20]

Participants

5

Reactant 3

HCID 702EthanolHCID 672641014-(1-methoxy-2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 575226211-Methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamineYield 97.4%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-(1-Methoxy-2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-morpholine (0.24 g, 0.00078 mol) was dissolved in ethanol (40 mL, 0.7 mol) and placed in a Parr bottle. To this solution was added palladium on carbon (10 mg). The reaction mixture was placed under 50 psi of hydrogen and shaken overnight. The mixture was filtered through celite and washed with additional ethanol (40 mL). The filtrate was concentrated in vacuo. The film was triturated with diethyl ether to provide 1-methoxy-7-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine as a solid (0.21 g, 97%). 1H NMR (400 MHz, CDCl3) δ 6.71 (d, 1H, J=7.84 Hz), 6.51 (d, 1H, J=7.83 Hz), 3.70 (s, 7H), 3.31 (m, 1H), 2.75 (m, 1H), 2.60 (m, 2H), 2.55 (s, 4H), 2.31 (m, 1H), 2.0-2.16 (m, 2H), 1.37 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with additional ethanol (40 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe film was triturated with diethyl ether

Sources & evidence

ORD record
ord-e8caa808609f401d948ead78b963907c
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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