trans-2-Phenyl-1-cyclopropanecarbonyl chloride → trans-(4-Cyclopropylpiperazin-1-yl)-(2-phenylcyclopropyl)methanone

HRID 572004Notes

Reaction equation

HRID 572004 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.Cl.Cl.[CH:15]1([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH2:17][CH2:16]1>>[CH:15]1([N:18]2[CH2:23][CH2:22][N:21]([C:10]([C@@H:8]3[CH2:9][C@H:7]3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[O:11])[CH2:20][CH2:19]2)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 13656trans-2-Phenyl-1-cyclopropanecarbonyl chlorideHCID 212208121-Cyclopropylpiperazine dihydrochloride

Product 1

HCID 25196564trans-(4-Cyclopropylpiperazin-1-yl)-(2-phenylcyclopropyl)methanone

Procedure

This example was prepared according to Example 4 employing trans-2-phenyl-1-cyclopropanecarbonyl chloride and 1-cyclopropylpiperazine dihydrochloride, which was prepared according to Gillaspy, et. al. Tetrahedron Lett. 1995, 36 (41), 7399-7402. m/z (ES+) M+1=271.2; HPLC tR=1.43 min. 1H NMR (500 MHz, CDCl3) δ 7.29-7.26 (m, 2H), 7.19 (d, J=7.3 Hz, 1H), 7.11 (d, J=7.0 Hz, 2H), 3.69-3.50 (m, 4H), 2.59 (t, J=5.2 Hz, 4H), 2.48 (ddd, J=8.9, 6.3, 4.3 Hz, 1H), 1.96 (ddd, J=8.2, 5.5, 4.3 Hz, 1H), 1.68-1.59 (m, 2H), 1.26 (ddd, J=8.4, 6.3, 4.3 Hz, 1H), 0.49-0.44 (m, 2H), 0.44-0.38 (m, 2H).

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-2f60732adb914beca919d96884c66689
Source dataset
uspto-grants-2015_05
Patent number
US09029381B2

Reaction notes

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