Hexylamine → HCID 22141162, compound
Reaction equation
Cl[CH2:2][CH:3]1[CH:5]([C:6]([O:8]CC)=O)[C:4]1([CH2:20][CH3:21])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1.C(=O)([O-])O.[Na+].[CH2:27]([NH2:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>>[CH2:20]([C:4]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:5]2[CH:3]1[CH2:2][N:33]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:6]2=[O:8])[CH3:21]Participants
Conditions
- Temperature
- 150 °C
Procedure
To a solution of ethyl 3-(chloromethyl)-2-ethyl-2-(3-nitrophenyl)cyclopropane carboxylate (Preparation 16, 4.0 g, 12.8 mmol), was added sodium hydrogen carbonate (1.3 g, 15.4 mmol) and hexylamine (15.3 g, 20 ml, 151 mmol). The mixture was heated to 150° C. for 12 h, then cooled to room temperature and partitioned between hydrochloric acid (2N, 500 ml) and ethyl acetate (2×500 ml). The combined organic layers were washed with water (500 ml), dried (MgSO4), filtered and concentrated in vacu0. The residue was purified by silica (200 g) column chromatography eluting with a gradient of dichloromethane/ethyl acetate 100:0 to 90:10. Product-containing fractions were combined and concentrated inl iacuo to give the title compound as an orange oil (1.4 g, 32%).
Workup
- temperaturecooled to room temperature
- custompartitioned between hydrochloric acid (2N, 500 ml) and ethyl acetate (2×500 ml)
- washThe combined organic layers were washed with water (500 ml)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacu0
- customThe residue was purified by silica (200 g) column chromatography
- washeluting with a gradient of dichloromethane/ethyl acetate 100:0 to 90:10
- concentrationconcentrated inl iacuo
Sources & evidence
- ORD record
- ord-da491e6726fe4776a013ed89849b57c5
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313312B1
Reaction notes
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