Réaction #1552110

ord-3472921a5b7c41b6a30dc01077da7322

Équation de réaction

O=C(O)c1cc(=O)[nH]c(=O)[nH]1
Orotic acid
O=C(O)c1cc(=O)[nH]c(=O)[nH]1
orotic acid
C[C@H]1CNCCc2ccc(Cl)cc21
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
CC(C)=O
acetone
→
C[C@H]1CNCCc2ccc(Cl)cc21.O=C(O)c1cc(=O)[nH]c(=O)[nH]1
(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt

Réactifs

O=C(O)c1cc(=O)[nH]c(=O)[nH]1
Orotic acid
O=C(O)c1cc(=O)[nH]c(=O)[nH]1
orotic acid
C[C@H]1CNCCc2ccc(Cl)cc21
(R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine
CC(C)=O
acetone

Réactifs

Aucun

Solvants

CC(C)O
isopropanol
CCOC(C)=O
ethyl acetate

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutrePrecipitation
  2. 2
    Températureto cool
  3. 3
    FiltrationThe resulting solid was recovered by filtration
  4. 4
    Autreair-dried in a fume hood overnight
  5. 5
    Autreby DSC of 236° C.

Mode opératoire

(R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt was prepared by addition of one equivalent of orotic acid to a solution of (R)-8-chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine in isopropanol, ethyl acetate, or acetone at 60° C. Orotic acid, at 60° C., was added drop-wise, in the corresponding solvent, with vigorous stirring. Precipitation occurred immediately and the suspension was allowed to cool and stir overnight. The resulting solid was recovered by filtration and air-dried in a fume hood overnight. (R)-8-Chloro-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine orotate salt had an extrapolated initial melting onset temperature by DSC of 236° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08999970B2uspto-grants-2015_04