Reaction #2186191

ord-18eefd571c03425384bca27ebde444a8

Reaction equation

O=Cc1ccc(N2CCN(CCF)CC2)cc1O
4-[4-(2-Fluoro-ethyl)-piperazin-1-yl]-2-hydroxy-benzaldehyde
COC(=O)Cc1nc2ccccc2s1
benzothiazol-2-yl-acetic acid methyl ester
C1CCNCC1
piperidine
O=c1oc2cc(N3CCN(CCF)CC3)ccc2cc1-c1nc2ccccc2s1
desired product
Yield 55.0%
O=c1oc2cc(N3CCN(CCF)CC3)ccc2cc1-c1nc2ccccc2s1
3-Benzothiazol-2-yl-7-[4-(2-fluoro-ethyl)-piperazin-1-yl]-chromen-2-one
Yield 55.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto reach room temperature
  2. 2
    Filtrationthe precipitate filtered off
  3. 3
    Washwashed with diethylether
  4. 4
    Otherdried under high vacuum

Procedure

200 mg (0.793 mmol) 4-[4-(2-Fluoro-ethyl)-piperazin-1-yl]-2-hydroxy-benzaldehyde and 164 mg (1 eq.) benzothiazol-2-yl-acetic acid methyl ester are heated to reflux for 3 h in 5 mL benzene and 2.5 mL acetonitrile, in the presence of 0.157 mL (2 eq.) piperidine. The reaction mixture is allowed to reach room temperature and the precipitate filtered off, washed with diethylether and dried under high vacuum to yield 90 mg (55%) of desired product as a yellow powder (melting point: 246° C.).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07569337B2uspto-grants-2009_08