2,6-Dichlorobenzothiazole → HCID 86607626, compound

HRID 1990797Notes

Reaction equation

HRID 1990797 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:14]1>C1COCC1>[CH2:22]([O:21][C:19]([N:16]1[CH2:15][CH2:14][CH:13]([NH:12][C:2]2[S:3][C:4]3[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:18][CH2:17]1)=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 771762,6-DichlorobenzothiazoleHCID 100867Ethyl 4-amino-1-piperidinecarboxylate

Product 1

HCID 86607626HCID 86607626, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,6-dichloro-benzothiazole (1.83 g, 8.97 mmol, 1.0 equiv) and ethyl 4-amino-1-piperidine carboxylate (3.09 g, 17.93 mmol, 2.0 equiv) in anhydrous THF (20 mL) was heated to reflux for 12 h. Purification with column chromatography on silica eluting with ethyl acetate/hexane (3:1) yielded 2.5 g (76%) of the title compound. 1H NMR (400 MHz, DMSO): δ 1.18 (t, J=7.2 Hz, 3H), 1.33 (br m, 2H), 1.97 (br d, 2H), 3.01 (br s, 2H), 3.90 (br d, 3H), 4.04 (q, J=7.2 Hz, 2H), 7.21 (m, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.78 (s, 1H), 8.16 (d, J=7.2 Hz, 1H). MS (ISP): 340.4 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. customPurification with column chromatography on silica eluting with ethyl acetate/hexane (3:1)

Sources & evidence

ORD record
ord-6d14b0ba343f41348a24725207bf5b36
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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