Sodium Azide → HCID 19980241, compound

HRID 1461277Notes

Reaction equation

S(O[CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[O:17][C:16]([C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)(C)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C)C=O>[N:26]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[O:17][C:16]([C:18]([N:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)=[N+:27]=[N-:28]

Participants

Conditions

Temperature: 120 °C

Procedure

In 90 ml of dimethylformamide were dissolved 4.04 g (10.9 mmol) of Compound u and 7.1 g (109.2 mmol) of sodium azide and the solution was heated at 120° C. for 1.5 hours. The reaction mixture was allowed to stand for cooling and, then, the insolubles were filtered off. The filtrate was concentrated under reduced pressure. The residue was diluted with 120 ml of ethyl acetate and washed with 3 portions of saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue was purified by silica gel column chromatography (chloroform-methanol=30:1) to give 2.28 g (65.9%) of 1-[5-(4-azidopiperidinomethyl)-2-furancarbonyl]piperidine (Compound v) as light yellow oil.

Workup

temperaturefor cooling
filtrationthe insolubles were filtered off
concentrationThe filtrate was concentrated under reduced pressure
additionThe residue was diluted with 120 ml of ethyl acetate
washwashed with 3 portions of saturated aqueous sodium chloride solution
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
distillationThe solvent was then distilled off
customthe residue was purified by silica gel column chromatography (chloroform-methanol=30:1)

Sources & evidence

ORD record: ord-4f49d79544fd47e9a9ebb86c76dd3ca6
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075301

Reaction notes

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