Ammonium formate → 4-(2-Ethyl-4,5,6,7-tetrahydro-2h-indazol-3-yl)piperidine

HRID 1068251Notes

Reaction equation

[CH2:1]([N:3]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][CH2:13]2)=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[N:4]1)[CH3:2].C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[CH2:1]([N:3]1[C:11]([CH:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[N:4]1)[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 0.273 g 4-(2-ethyl-4,5,6,7-tetrahydro-2H-indazol-3-yl)-1-benzylpiperidine from Step B above, 0.789 g ammonium formate, and 35 mg 20% Pd(OH)2 in 6 mL MeOH was heated at 65° C. for 1 hour. Basic aqueous work-up with ether extraction provided 0.192 g title compound as a colorless solid (97%). 1H NMR (500 MHz) δ 4.08 (q, 7.2 Hz, 2H), 3.19 (br d, 11.9 Hz, 2H), 2.71˜2.77 (m, 1H), 2.68˜2.74 (m, 2H), 2.64˜2.66 (m, 2H), 2.60˜2.62 (m, 2H), 1.82˜1.91 (m, 2H), 1.71˜1.80 (m, 6H), 1.40 (t, 7.2 Hz, 3H). The identity of the title compound was confirmed again by NOE difference spectroscopy.

Workup

extractionBasic aqueous work-up with ether extraction

Sources & evidence

ORD record: ord-bd66d23eb0024892bb9a265c7c63452c
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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