Ammonia → 4-Piperidin-1-ylindan-1-ylamine

HRID 451621Notes

Reaction equation

HRID 451621 reaction equation
CO[N:3]=[C:4]1[C:12]2[C:7](=[C:8]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.N>CO.[Ni]>[N:13]1([C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:7]=2[CH2:6][CH2:5][CH:4]3[NH2:3])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 865966744-Piperidin-1-ylindan-1-one O-methyloxime

Product 1

HCID 671879554-Piperidin-1-ylindan-1-ylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

4-Piperidin-1-ylindan-1-one O-methyloxime (4.33 g, 17.7 mmol) was added to a mixture of 20% ammonia in methanol (200 mL) and Raney 2800 nickel (43 g) in a stainless steel autoclave. The reactor was sealed and flushed with nitrogen, and then it was pressurized with hydrogen (60 psi). The mixture was stirred at ambient temperature for 90 minutes. The Raney nickel was filtered off, washed with methanol and the filtrate was concentrated. Obtained 4-piperidin-1-ylindan-1-yl-amine (3.81 g, 99%) as a yellow oil. MS (DCI/NH3) m/z: 217.13 [M+H]+. 1H NMR (DMSO-d6) δ: 1.51 (m, 3H), 1.62 (m, 4H), 1.77 (s, 2H), 2.28 (m, 1H), 2.62 (m, 1H), 2.80 (m, 3H), 2.94 (m, 2H), 4.14 (t, 1H), 6.71 (d, 1H), 6.95 (d, 1H), 7.09 (t, 1H).

Workup

  1. customThe reactor was sealed
  2. customflushed with nitrogen
  3. filtrationThe Raney nickel was filtered off
  4. washwashed with methanol
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2781939ca29b497fac4378c5fc4ce759
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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