Sodium Hydroxide → Sodium [2-(6-piperidinohexyl)amino-2-oxoethoxy]acetate
Reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[C:18](=[O:19])[CH2:17][O:16][CH2:15][C:14]2=[O:20])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:21].[Na+:22]>>[N:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[CH2:15][O:16][CH2:17][C:18]([O-:21])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1.[Na+:22]Participants
Procedure
To a mixture of 3.63 grams (9.84 millimoles) of 6-(3,5-dioxomorpholino)hexyl p-toluenesulfonate (prepared as described in Example IX) and 84.75 milligrams (10.7 millimoles) of lithium hydride in 10 milliliters of 1,2-dimethoxyethane was added 1.0 milliliter (10.0 millimoles) of piperidine in 10 milliliters of 1,2-dimethoxyethane. The mixture was heated under reflux for 22 hours, and the resulting heterogeneous mixture filtered to obtain a clear yellow filtrate. The filtrate was concentrated to an orange oil which after evaporative distillation (bath 120° C.; 0.05 torr.) produced 1.18 grams (42.5 percent yield) of 4-(6-piperidinohexyl)-3,5-dioxomorpholine base having infrared and nuclear magnetic resonance spectral characteristics appropriate for said compound. A 286.23 milligram (1.02 millimoles) sample of the free base, 4-(6-piperidinohexyl)-3,5-dioxomorpholine, was dissolved in 1.0 milliliter of 1 N sodium hydroxide (1.0 millimole) and the mixture concentrated to produce 289.63 grams (90 percent yield) of sodium [2-(6-piperidinohexyl)amino-2-oxoethoxy]acetate product with the following spectral characteristics:
Workup
- concentrationthe mixture concentrated
Sources & evidence
- ORD record
- ord-a03aa48555b1434aa27e02a6d0806697
- Source dataset
- uspto-grants-1980_04
- Patent number
- US04197315
Reaction notes
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