2-Diisopropylaminoethanol → HCID 23294900, compound

HRID 1955284Notes

Reaction equation

[C:1]1([C:7]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:18].[CH:20]([N:23]([CH:27]([CH3:29])[CH3:28])[CH2:24][CH2:25]O)([CH3:22])[CH3:21]>>[ClH:18].[C:1]1([C:7]2([C:13]([O:15][CH2:25][CH2:24][N:23]([CH:27]([CH3:29])[CH3:28])[CH:20]([CH3:22])[CH3:21])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Reactant 3

HCID 73132-Diisopropylaminoethanol

HCID 24386Thionyl Chloride

HCID 708171-Phenylcyclohexane-1-carboxylic acid

Product 1

HCID 23294900HCID 23294900, compound

Conditions

Temperature: 80 °C

Procedure

1-Phenyl-cyclohexanecarboxylic acid (1 g, 4.9 mmol) was refluxed with SOCl2 (15 mL). After 0.5 h, the reaction mixture was evaporated and the residue was dissolved in toluene. 2-Diisopropylaminoethanol (1.4 g, 9.8 mmol) was added and the mixture was stirred at 80° C. for 14 h. The reaction mixture was filtered and chromatographed on silica gel using toluene-Et3N 95:5 as eluent. The yield was 1.5 g (84%); mp 119-122° C.; 1H NMR (D2O) δ 1.38 (d, 12H), 1.40 (m, 1H), 1.54 (m, 2H), 1.63-1.76 (m, 3H), 1.95 (t, 2H), 2.45 (d, 2H), 3.44 (t, 2H), 3.67 (m, 2H), 4.44 (t, 2H), 7.43 (t, 1H), 7.51 (t, 2H), 7.54 (d, 2H). Anal. (C21H33NO2.HCl) C, H, N.

Workup

customthe reaction mixture was evaporated
dissolutionthe residue was dissolved in toluene
filtrationThe reaction mixture was filtered
customchromatographed on silica gel

Sources & evidence

ORD record: ord-b360d15251334d42b84aa4081ef0bed7
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124354

Reaction notes

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