Cyclohexanone → HCID 12994076, compound

HRID 1581759Notes

Reaction equation

HRID 1581759 reaction equation
[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:8]1([C:14]2[CH:27]=[CH:26][C:25]3[C:16](=[C:17]4[C:22](=[CH:23][CH:24]=3)[CH:21]=[CH:20][CH:19]=[N:18]4)[N:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>>[CH:8]1([C:14]2[CH:27]=[CH:26][C:25]3[C:16](=[C:17]4[C:22](=[CH:23][CH:24]=3)[CH:21]=[CH:20][C:19]([C:1]3([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:18]4)[N:15]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 7967CyclohexanoneHCID 12994073HCID 12994073, compound

Product 1

HCID 12994076HCID 12994076, compoundYield 60%

Procedure

By following General Procedure I, cyclohexanone (0.094 g, 0.953 mmol) was added to 2-(cyclohexyl)-1,10-phenanthroline, prepared as described by Example 15, (0.100 g, 0.381 mmol) and 0.1 M SmI2 (8.38 mL, 0.838 mmol) yielding 0.083 g (60% yield) of the title compound as a colorless oil: 1H NMR (300 MHz, CDCl3) δ8.24 and 8.14 (two d, J=8.40 Hz, Hp3 and Hp9), 7.76 and 7.70 (two d, J=8.80 Hz, Hp5 and Hp6), 7.66 and 7.52 (two d, J=8.40 Hz, Hp4 and Hp7), 3.06 (tt, J=11.85, 3.30 Hz, (CH2)5CH (phenan)), 2.18-1.74 (m, 10H), 1.52-1.33 (m, 10H); 13C NMR (75 MHz) δ166.98, 165.25, 144.88, 143.44, 137.16, 136.01, 127.49, 127.28, 126.21, 124.85, 121.47, 118.65, 73.16, 47.24, 36.75, 32.81, 26.64, 26.12, 25.75, 22.71; IR (CHCl3) 3338 (OH), 3042 (C—H Ar), 2927 (CH), 852 (C—H Ar) cm−1; HRMS m/e Calcd for C24H29N2O (MH+): 361.2280, found, 361.2272.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-8c0cf30c29cb4d999791e6af0889780c
Source dataset
uspto-grants-2004_05
Patent number
US06730788B1

Reaction notes

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