Piperidine → HCID 66905916, compound

HRID 2040976Notes

Reaction equation

CS(O[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[S:13][C:14]3[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:15]=3[N:16]=2)[CH2:7]1)(=O)=O.[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[N:22]1([C@H:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]3[S:13][C:14]4[CH:20]=[C:19]([Br:21])[CH:18]=[CH:17][C:15]=4[N:16]=3)[CH2:7]2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

Reactant 2

HCID 8082Piperidine

HCID 57747913HCID 57747913, compound

Product 1

HCID 66905916HCID 66905916, compoundYield 24%

Procedure

The title compound was prepared by the method of Example 34, substituting (R)-1-(6-bromobenzo[d]thiazol-2-yl)piperidin-3-yl methanesulfonate (Reference Example 12) in place of (S)-1-(6-bromobenzo[d]thiazol-2-yl)piperidin-3-yl methanesulfonate (Reference Example 10) and substituting piperidine in place of azetidine to give (S)-2-(1,3′-bipiperidin-1′-yl)-6-bromobenzo[d]thiazole (0.018 g, 24% yield). 1H NMR (300 MHz, CD3OD) δ ppm 1.45-1.55 (m, 2H), 1.56-1.73 (m, 6H), 1.82-1.95 (m, 1H), 2.04-2.12 (m, 1H), 2.46-2.57 (m, 1H), 2.59-2.74 (m, 4H), 3.04-3.18 (m, 2H), 3.96-4.05 (m, 1H), 4.22-4.30 (m, 1H), 7.33 (d, J=9 Hz, 1H), 7.39 (dd, J=2, 9 Hz, 1H), 7.79 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 380 (M+H)+.

Workup

customThe title compound was prepared by the method of Example 34

Sources & evidence

ORD record: ord-5134ac3941974b429973da794ae50372
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08580968B2

Reaction notes

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