Sodium Azide → Benzyl 4-(2-azidoacetyl)morpholine-2-carboxylate

HRID 253145Notes

Reaction equation

HRID 253145 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1)=[O:4].[N-:21]=[N+:22]=[N-:23].[Na+]>>[N:21]([CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1)=[O:4])=[N+:22]=[N-:23]

Participants

3

Reactant 2

HCID 33557Sodium AzideHCID 66844936Benzyl 4-(2-chloroacetyl)morpholine-2-carboxylate

Product 1

HCID 86614022Benzyl 4-(2-azidoacetyl)morpholine-2-carboxylateYield 86.4%

Procedure

In a 25-mL round-bottom flask, the benzyl 4-(2-chloroacetyl)morpholine-2-carboxylate (0.262 g, 0.88 mmol) was dissolved in dmf (4 mL). Sodium azide (0.066 g, 1.0 mmol) was added, and the flask was placed in a 60 deg oil bath overnight. The reaction was concentrated, and the residue was taken up in 80% ether-hexane (60 mL) and the organic layer was extracted with dilute sodium bicarbonate (2×7 mL) then with saturated brine (7 mL), then was dried over magnesium sulfate, filtered, and concentrated. The residue was purified through silica gel (50 mL) which had been deactivated with TEA (5 mL) using 60% EtOAc-hexane to afford the title compound (230 mg, 0.76 mmol). MS m/z 305 (M+1).

Workup

  1. customwas placed in a 60 deg
  2. customovernight
  3. concentrationThe reaction was concentrated
  4. extractionthe organic layer was extracted with dilute sodium bicarbonate (2×7 mL)
  5. dry with materialwith saturated brine (7 mL), then was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified through silica gel (50 mL) which

Sources & evidence

ORD record
ord-6ca5978938564430b5e2adb4f04610cb
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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