Tert-Butylamine → HCID 12532695, compound
Reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7]([NH2:11])([CH3:10])([CH3:9])[CH3:8]>C(OCC)C.CCCCC.[Ti](Cl)(Cl)(Cl)Cl>[C:7]([N:11]=[C:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([CH3:10])([CH3:9])[CH3:8]Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -55 °C
Procedure
Cyclopentanone (13.3 mL, 150 mmol) and tert-butylamine (47.4 mL, 450 mmol) were combined in 110 mL diethyl ether under a nitrogen atmosphere and were then cooled to −55° C. in a dry ice/acetonitrile bath. Titanium tetrachloride (8.2 mL, 75 mmol) was taken up in 70 mL pentane and added dropwise to the above solution, being careful to maintain the temperature at −40° C. the reaction was then stirred at −40° C. for 6 h and was then allowed to warm to room temperature overnight. The reaction mixture was filtered through a short plug of celite and washed with diethyl ether. The filtrate was evaporated in vacuo to yield 15.9 g (76%) of the title product as a clear oil.
Workup
- additionadded dropwise to the above solution
- temperatureto maintain the temperature at −40° C. the reaction
- temperatureto warm to room temperature overnight
- filtrationThe reaction mixture was filtered through a short plug of celite
- washwashed with diethyl ether
- customThe filtrate was evaporated in vacuo
Sources & evidence
- ORD record
- ord-0f1a0d1a249d4cc99b9629c4f0dfa994
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07691877B2
Reaction notes
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