trans-2-Phenyl-1-cyclopropanecarbonyl chloride → HCID 25196561, compound

HRID 572001Notes

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.[CH:13]1([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>>[CH:13]1([N:19]2[CH2:24][CH2:23][N:22]([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])[CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

Reactant 2

HCID 13656trans-2-Phenyl-1-cyclopropanecarbonyl chloride

HCID 872981-Cyclohexylpiperazine

Product 1

HCID 25196561HCID 25196561, compound

Procedure

This example was prepared according to Example 1 by employing trans-2-phenyl-1-cyclopropanecarbonyl chloride and 1-cyclohexylpiperazine, which is commercially available from, for example, Sigma-Aldrich Corporation, to afford title compound as a white solid. m/z (ES+) M+1=313.2; HPLC tR=1.76 min. 1H NMR (500 MHz, CDCl3) □7.28-7.24 (m, 2H), 7.19-7.15 (m, 1H), 7.10 (d, J=7.9 Hz, 2H), 3.67-3.53 (m, 4H), 2.58-2.49 (m, 4H), 2.47 (dt, J=8.9, 1.3 Hz, 1H), 2.29-2.22 (m, 1H), 2.00-1.92 (m, 1H), 1.79 (dd, J=17.7, 3.4 Hz, 4H) 1.66-1.58 (m, 2H) 1.26-1.16 (m, 5H) 1.15-1.0 (m, 1H).

Sources & evidence

ORD record: ord-d10c2b7f09304f24ba6a3dc25857b560
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029381B2

Reaction notes

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