Triethylamine → 1-(1,4-Dioxaspiro[4,5]dec-8-ylacetyl)-4-(2-pyridinyl)piperazine
Reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][C:12]([OH:14])=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>ClCCl>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([CH2:11][C:12]([N:39]3[CH2:40][CH2:41][N:36]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=4)[CH2:37][CH2:38]3)=[O:14])[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
An ice-cold solution of 1,4-dioxaspiro[4,5]-decane-8-acetic acid (20.0 g) (Example G) and triethylamine (20.9 ml) in 100 ml of dichloromethane is treated dropwise with a solution of isobutyl chloroformate (19.4 ml) in 100 ml of dichloromethane under nitrogen. The resulting solution is stirred at 0° C. for 10 minutes and a solution of 1-(2-pyridyl)-piperazine (32.59 g) in 100 ml of dichloromethane is added dropwise. The mixture is stirred at 0° C. for 15 minutes and then at room temperature for one hour. After washing with 1 L of a saturated solution of sodium bicarbonate, the organic phase is dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by MPLC (silica; ethyl acetate) to give 25.50 g of the title compound as a colorless solid; mp 113°-116° C.
Workup
- stirringThe mixture is stirred at 0° C. for 15 minutes
- waitat room temperature for one hour
- washAfter washing with 1 L of a saturated solution of sodium bicarbonate
- dry with materialthe organic phase is dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe crude product is purified by MPLC (silica; ethyl acetate)
Sources & evidence
- ORD record
- ord-f855816bccda45eb85e77de550946b54
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04988699
Reaction notes
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