Sodium Azide → HCID 86727622, compound

HRID 519211Notes

Reaction equation

[CH:1]([N:14]1[CH2:17][C:16](Cl)([CH3:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[N:20]([C:16]1([CH3:18])[CH2:17][N:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15]1)=[N+:21]=[N-:22]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-benzhydryl-3-chloro-3-methyl-azetidine (2 g, 7.39 mmol) and NaN3 (0.8 g, 12.31 mmol) was dissolved in DMF (30 mL) and the mixture was stirred at 100° C. overnight. The mixture was cooled to ambient temperature and partitioned between water (150 mL) and DCM (50 mL). The organic phase was washed with brine (3×30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo to give 3-azido-1-benzhydryl-3-methyl-azetidine as a yellow oil (2.1 g, 100%), which was used directly in the next step. LC/MS (Table 1, Method 2) Rt=0.915 min; MS m/z: 279 [M+H]+

Workup

temperatureThe mixture was cooled to ambient temperature
custompartitioned between water (150 mL) and DCM (50 mL)
washThe organic phase was washed with brine (3×30 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1c41ded913df4d59837f77313022e577
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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