Hydrochloric Acid → HCID 19906292, compound

HRID 2371707Notes

Reaction equation

HRID 2371707 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+].[ClH:37]>O.CN(C)C=O>[ClH:37].[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[C:16]3[CH2:17][CH2:18][N:19]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:20][CH2:21]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 1201458Desloratadine impurity 24

Product 1

HCID 19906292HCID 19906292, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3.00 g of 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, 2.34 g of ethyl 4-bromobutyrate, 1.51 g of potassium carbonate and 18 ml of N,N-dimethylformamide was stirred at 70° C. for 3 hrs. After cooling, water was added to the reaction mixture and then extracted with ether. The ether layer was washed with water, dried and concentrated to give pale brown solid, which was converted to the hydrochloride in the usual manner to give 3.88 g of colorless solid. The crude hydrochloride was recrystallized from a mixture of acetone and ether to give colorless crystals, mp 182°-184° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. washThe ether layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto give pale brown solid, which

Sources & evidence

ORD record
ord-78cb6426b0f4468db0857e589caf1602
Source dataset
uspto-grants-1992_03
Patent number
US05095022

Reaction notes

Loading…