Ethylmorpholine → HCID 21709325, compound

HRID 651792Notes

Reaction equation

[C:1]([N:6]1[CH2:11][CH2:10][C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])(C(O)=O)[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].C([N:22]1[CH2:27]COCC1)C.ClC(OCC(C)C)=[O:30].[N-]=[N+]=[N-].[Na+]>O1CCCC1.O.C1(C)C=CC=CC=1>[C:1]([N:6]1[CH2:7][CH2:8][C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])([N:22]=[C:27]=[O:30])[CH2:10][CH2:11]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1.25 g of 1,4-dicarbethoxypiperidine-4-carboxylic acid in 10 ml of dry tetrahydrofuran was cooled to ice temperature and was treated with 0.7 ml of N-ethylmorpholine then 0.7 ml of isobutyl chloroformate. The mixture was stirred at ice temperature for 20 minutes and then a solution of 0.59 g of sodium azide in 7 ml of water added. The mixture was stirred at ice temperature for 15 minutes and then at room temperature for a further 30 minutes. The mixture was then shaken with 20 ml of toluene and the toluene extract washed with a further portion of water and then with saturated sodium chloride solution. After drying over anhydrous magnesium sulphate the toluene solution was reduced to approximately half its volume and then heated at 100° C. for 1 hour. The toluene was evaporated and there was obtained 1.148 g of 1,4-dicarbethoxy-4-isocyanatopiperidine in the form of an oil.

Workup

stirringThe mixture was stirred at ice temperature for 15 minutes
waitat room temperature for a further 30 minutes
extractionthe toluene extract
washwashed with a further portion of water
dry with materialAfter drying over anhydrous magnesium sulphate the toluene solution
customThe toluene was evaporated

Sources & evidence

ORD record: ord-375ae3b6d89c46fcbaffffe91bd82a43
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06281363B1

Reaction notes

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