Allylamine → HCID 68577026, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8](O)[CH2:9][N:10]([CH2:14][CH2:15]O)[CH2:11][CH:12]=[CH2:13])=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:30]([NH2:33])[CH:31]=[CH2:32].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:9][N:10]([CH2:11][CH:12]=[CH2:13])[CH2:14][CH2:15][N:33]2[CH2:30][CH:31]=[CH2:32])=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 5 °C
Procedure
To (R)-1-(4-chlorophenyl)-2-[(2-hydroxyethyl)(2-propenyl)amino]-1-ethanol (724 mg, 2.5 mmol) produced in Example 13, tetrahydrofuran (2.51 g) and triethylamine (868 mg, 3.5 equivalents) were added. The mixture was cooled to 5° C. Methanesulfonyl chloride (899 mg, 3.2 equivalents) was added dropwise thereto, and then allylamine (839 mg, 6.0 equivalents) was added dropwise thereto. The temperature of the mixture was raised to 25° C., and then the mixture was stirred for 12 hours. To the mixture, 10 wt % aqueous solution of sodium carbonate (4.15 g) was added. After the organic layer and aqueous layer were separated, the aqueous layer was extracted with toluene (5 mL). The organic layers were combined, and washed twice with distilled water (5 mL). The obtained organic layer was concentrated and dried under vacuum, to obtain 709 mg of the title compound as pale yellow oil (yield: 92%, chemical purity: 81.7 area %).
Workup
- temperatureThe temperature of the mixture was raised to 25° C.
- customAfter the organic layer and aqueous layer were separated
- extractionthe aqueous layer was extracted with toluene (5 mL)
- washwashed twice with distilled water (5 mL)
- concentrationThe obtained organic layer was concentrated
- customdried under vacuum
Sources & evidence
- ORD record
- ord-cd63bd6ceaee42a6aebbf1f3166254c4
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273883B2
Reaction notes
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