Triethylamine → HCID 118024938, compound
Reaction equation
[CH2:1]([N:4]([CH2:21][CH:22]=[CH2:23])[CH:5]1[CH2:9][CH:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][CH:6]1O)[CH:2]=[CH2:3].C([N:26](CC)CC)C.CS(Cl)(=O)=O.[OH-].[NH4+]>CC(OC)(C)C>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][O:10][CH:8]2[CH2:9][CH:5]([N:4]([CH2:21][CH:22]=[CH2:23])[CH2:1][CH:2]=[CH2:3])[CH:6]([NH2:26])[CH2:7]2)=[CH:13][CH:14]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-[bis(prop-2-en-1-yl)amino]-4-[(4-methoxyphenyl)methoxy]cyclopentan-1-ol (8.75 g, 27.6 mmol) in dry MTBE (92 ml) at 0° C. under nitrogen was added triethylamine (7.68 ml, 55.1 mmol) and methanesulfonyl chloride (2.58 ml, 33.1 mmol). The reaction mixture was stirred at 0° C. for 30 minutes. To this was then added further triethylamine (7.68 ml, 55.1 mmol) and the reaction was stirred at 0° C. for 30 minutes followed by the addition of ammonium hydroxide (25% aq, 82 ml, 590 mmol). The reaction was warmed to room temperature for 17 hours then partitioned between MTBE and water. The aqueous layer was re-extracted with MTBE. The combined organics were dried over magnesium sulphate, filtered and concentrated in vacuo to afford the title compound.
Workup
- stirringthe reaction was stirred at 0° C. for 30 minutes
- temperatureThe reaction was warmed to room temperature for 17 hours
- customthen partitioned between MTBE and water
- extractionThe aqueous layer was re-extracted with MTBE
- dry with materialThe combined organics were dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8905b0548d1b438caf5c37977dea69c9
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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