Sodium Azide → trans-{3-Azidomethyl-1-[2-(4-fluoro-phenyl)-ethyl]-piperidin-4-yl}-benzyl-methylamine

HRID 896555Notes

Reaction equation

[CH2:1]([N:8]([CH3:30])[C@@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:11][C@H:10]1[CH2:24]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:31]([CH2:24][C@H:10]1[C@H:9]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:30])[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:11]1)=[N+:32]=[N-:33]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of crude methanesulfonic acid trans-4-(benzyl-methyl-amino)-1-[2-(4-fluorophenyl)-ethyl]-piperidin-3-ylmethyl ester (139 mg, 294 μmol) and sodium azide (58 mg, 882 μmol) in N,N-dimethylformamide (2 mL) was heated at 60° C. for 20 hours, then cooled to room temperature. The mixture was diluted with ethyl acetate, washed three times with water, dried over sodium sulfate, and concentrated under vacuum to provide a gum (106 mg, 95%) which was used without purification. 1H NMR (300 MHz, CDCl3) δ7.33 (m, 5H), 7.16 (m, 2H), 6.99 (t, J=9 Hz, 2H), 3.70 (m, 2H), 3.52 (d, J=13 Hz, 1H), 3.41 (m, 1H), 3.20 (m, 2H), 2.83 (m, 2H), 2.61 (m, 2H), 2.42 (m, 1H), 2.3-1.8 (m, 4H), 2.19 (s, 3H), 1.75 (m, 1H).

Workup

temperaturecooled to room temperature
washwashed three times with water
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-6e7dcf28f02f4de0a37d63633807e8a3
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919356B2

Reaction notes

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