Ethyl Acetate → 4-(3-(3,4-Difluorobenzyl)-1-ethyl-(1H-pyrazol-5-yl))-1-benzyl-piperidine

HRID 1068140Notes

Reaction equation

HRID 1068140 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[CH2:15][C:16](=O)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C(O)=O.[CH2:34]([NH:36][NH2:37])[CH3:35].CCOC(C)=O>CCN(CC)CC>[F:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[F:24])[CH2:17][C:16]1[CH:15]=[C:14]([CH:11]2[CH2:12][CH2:13][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10]2)[N:36]([CH2:34][CH3:35])[N:37]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 211929941-(1-Benzylpiperidin-4-yl)-4-(3,4-difluorophenyl)butane-1,3-dione

Product 1

HCID 211929814-(3-(3,4-Difluorobenzyl)-1-ethyl-(1H-pyrazol-5-yl))-1-benzyl-piperidine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The title compound was prepared from 1-(1-benzylpiperidin-4-yl)-4-(3,4-difluorophenyl)butane-1,3-dione and ethylhydrazine oxalate using a procedure similar to that described in Example 1, Step B. RF: 0.29 (2:1 EtOAc to hexanes with 1% (v/v) Et3N). It was the fast-eluting isomer on silica gel. 1H NMR (500 MHz, CDCl3): δ7.29˜7.33 (m, 4H), 7.23˜7.28 (m, 1H), 7.05˜7.14 (m, 2H), 6.97˜7.01 (m, 1H), 5.86 (s, 1H), 4.06 (q, 7.2 Hz, 2H), 3.84 (s, 2H), 3.55 (s, 2H), 2.97 (br d, 11.9 Hz, H), 2.64 (tt, 12.1 & 3.7 Hz, 1H), 2.12˜2.16 (m, 2H), 1.83 (br d, 13.1 Hz, 2H), 1.62˜1.71 (m, 2H), 1.35 (t, 7.2 Hz, 3H); ESI-MS 396.2 (M+H), HPLC A: 3.43 min., compared with 3.54 min. for its isomer.

Sources & evidence

ORD record
ord-7723ecb8763c480abbc7b313603b8d95
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

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