Reaction #1007

ord-2a631a89ec7e4caea3676f4cb6dcf4c2

Reaction equation

Cc1nc2n(c(=O)c1CCN1CCC(c3noc4cc(F)ccc34)CC1)CCCC2
3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one
O=C(O)c1cc2ccccc2c(Cc2c(O)c(C(=O)O)cc3ccccc23)c1O
pamoic acid
Cc1nc2n(c(=O)c1CCN1CCC(c3noc4cc(F)ccc34)CC1)CCCC2.O=C(O)c1cc2ccccc2c(Cc2c(O)c(C(=O)O)cc3ccccc23)c1O
3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 4,4'-methylenebis[3-hydroxy-2-naphthalenecarboxylate]
Yield 81.0%

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe resulting precipitate was filtered off by suction
  2. 2
    Washwashed with ethanol
  3. 3
    Otherdried

Procedure

A solution of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one (0.048mol) in ethanol (600ml) was added to a solution of pamoic acid (0.048mol) in N,N-dimethylformamide (400ml). The mixture was stirred for 3 hours. The resulting precipitate was filtered off by suction, washed with ethanol and dried, yielding 31 g (81%) of 3-[2-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]ethyl]-6,7,8,9-tetrahydro-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one 4,4'-methylenebis[3-hydroxy-2-naphthalenecarboxylate](1:1); mp. 269.2° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723467uspto-grants-1998_03