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

HRID 656453Notes

Reaction equation

HRID 656453 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-e43b38f977be496bad883c9593fd4096
Source dataset
uspto-grants-2011_12
Patent number
US08071762B2

Reaction notes

Loading…