trans-2-Phenyl-1-cyclopropanecarbonyl chloride → trans-(2-Phenylcyclopropyl)-(4-propylpiperazin-1-yl)methanone

HRID 572006

Reaction equation

HRID 572006 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.Br.[CH2:15]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH2:16][CH3:17]>>[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10]([N:21]2[CH2:22][CH2:23][N:18]([CH2:15][CH2:16][CH3:17])[CH2:19][CH2:20]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 13656trans-2-Phenyl-1-cyclopropanecarbonyl chlorideHCID 3085288N-Propylpiperazinium dibromide

Product 1

HCID 25196674trans-(2-Phenylcyclopropyl)-(4-propylpiperazin-1-yl)methanone

Procedure

This example was prepared according to Example 4 utilizing trans-2-phenyl-1-cyclopropanecarbonyl chloride and 1-N-propylpiperazine dihydrobromide, which is commercially available from, for example, Sigma-Aldrich Corporation. m/z (ES+) M+1=273.2; HPLC tR=1.49 min. 1H NMR (500 MHz, CDCl3) δ 7.26 (t, J=7.6 Hz, 2H), 7.20-7.15 (m, 1H), 7.10 (d, J=7.0 Hz, 2H), 3.70-3.55 (m, 4H), 2.49-2.35 (m, 5H), 2.33-2.27 (m, 2H), 1.99-1.91 (m, 1H), 1.65 (dt, J=9.2, 4.7 Hz, 1H), 1.50 (sextet, J=7.5 Hz, 2H), 1.25 (ddd, J=8.4, 6.3, 4.3 Hz, 1H), 0.90 (t, J=7.3 Hz, 3H).

Sources & evidence

ORD record
ord-5461f64c8b7f4257ba29e43992955534
Source dataset
uspto-grants-2015_05
Patent number
US09029381B2

Linked notes

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