trans-2-Phenyl-1-cyclopropanecarbonyl chloride → HCID 25196567, compound

HRID 572008Notes

Reaction equation

HRID 572008 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.[C:13]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]>>[C:13]([N:17]1[CH2:22][CH2:21][N:20]([C:10]([C@@H:8]2[CH2:9][C@H:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:11])[CH2:19][CH2:18]1)([CH3:16])([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 13656trans-2-Phenyl-1-cyclopropanecarbonyl chlorideHCID 35305721-Tert-butylpiperazine

Product 1

HCID 25196567HCID 25196567, compound

Procedure

This example was prepared according to Example 1 employing trans-2-phenyl-1-cyclopropanecarbonyl chloride and 1-tert-butylpiperazine, which is commercially available from, for example, Beta Pharma. m/z (ES+) M+1=287.2; HPLC tR=1.60 min. 1H NMR (500 MHz, CDCl3) δ 7.34-7.23 (m, 2H), 7.23-7.15 (m, 1H), 7.11 (d, J=7.0 Hz, 2H), 3.73-3.53 (m, 4H), 2.64-2.50 (m, 4H), 2.47 (ddd, J=8.9, 6.4, 4.3 Hz, 1H), 1.96 (td, J=4.5, 3.5 Hz, 1H), 1.65 (ddd, J=9.2, 5.2, 4.3 Hz, 1H), 1.25 (ddd, J=8.2, 6.4, 4.3 Hz, 1H), 1.06 (s, 9H).

Sources & evidence

ORD record
ord-54dfe214d38348899c9bd3495fb75766
Source dataset
uspto-grants-2015_05
Patent number
US09029381B2

Reaction notes

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