1-Bromohexadecane → HCID 86587667, compound
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[CH2:18]([NH2:36])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]/[CH:26]=[CH:27]\[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:2]([CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]/[CH:27]=[CH:26]\[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][NH2:36])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
1-bromohexadecane (15.27 g, 50 mmol) was rapidly added to oleylamine (26.75 g, 100 mmol) at 100° C. The reaction mixture was heated at 120° C. for 30 minutes and than cooled to room temperature. Chloroform(200 ml) was added followed by 1 N NaOH (50 ml). The mixture was then extracted with H2O (200 ml), the organic layer dried (Na2SO4) and concentrated to a syrup. Silica gel column chromatography using 5-20% gradient methanol in dichloromethane afforded 20.5 g of palmityloleylamine as a syrup (yield, 83%). The identity of the product was confirmed using NMR spectroscopy. 1H NMR (CDCl3) d 5.34 (m, 2H, CH═CH), 2.58 (m, 4H), 2.00 (m, 4H), 1.47 (m, 4H), 1.25 (m, 48H), 0.86 (m, 6H). FAB-MS: 493 [M+H]+. (Other reagents could include oleyl-bromide and hexadecane amine)
Workup
- temperaturethan cooled to room temperature
- extractionThe mixture was then extracted with H2O (200 ml)
- dry with materialthe organic layer dried (Na2SO4)
- concentrationconcentrated to a syrup
- customafforded
Sources & evidence
- ORD record
- ord-14221c6c551142929850ebf9a6568799
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07553830B2
Reaction notes
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