Dichloromethane → HCID 70357721, compound

HRID 1709729Notes

Reaction equation

HRID 1709729 reaction equation
[CH2:1]1[C:10]2=[CH:11][CH2:12][CH2:13][C:8]3=[C:9]2[N:3]([CH:4]=[CH:5][CH2:6][CH2:7]3)[N:2]1[C:14]([OH:16])=O.[NH2:17][CH:18]1[CH:23]2[CH2:24][CH2:25][N:20]([CH2:21][CH2:22]2)[CH2:19]1.[OH-].[Na+].C(Cl)[Cl:29]>S(Cl)(Cl)=O>[ClH:29].[N:20]12[CH2:25][CH2:24][CH:23]([CH2:22][CH2:21]1)[CH:18]([NH:17][C:14]([N:2]1[N:3]3[C:9]4[C:10](=[CH:11][CH2:12][CH2:13][C:8]=4[CH2:7][CH2:6][CH:5]=[CH:4]3)[CH2:1]1)=[O:16])[CH2:19]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 1232383-AminoquinuclidineHCID 67928605HCID 67928605, compound

Product 1

HCID 70357721HCID 70357721, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
20 °C

Procedure

0.75 g (3.5 mmol) of 6,7,8,9-tetrahydro-pyrazolo[4,5,1-jk][1]benzazepine-2-carboxylic acid were boiled for 3 hours in 12 ml of thionyl chloride. Access of thionyl chloride was then removed by distillation under reduced pressure. 10 ml of toluene were added, and distillation under reduced pressure was repeated. The residue was dissolved in 10 ml of acetonitrile, and 0.83 g (6.6 mmol) of 3-amino-quinuclidine were added. The mixture was stirred for 18 hours at 20° C., then shaken with 2N sodium hydroxide and with methylene chloride. The methylene chloride layer was washed with water, dried and evaporated. The residue was dissolved in a mixture of 5 ml of absolute alcohol and 5 ml of ethyl acetate. The reaction mixture of 0.65 ml of acetyl chloride with 2 ml of absolute alcohol was added to the obtained solution and kept at 0° C. for 18 hours. The solid was then sucked off, washed with ethyl acetate and dried. In this manner 1.12 g of the desired product was obtained. The product decomposed slowly at 280° C. 13C NMR (CDCl3, ref: TMS)

Workup

  1. customAccess of thionyl chloride was then removed by distillation under reduced pressure
  2. addition10 ml of toluene were added
  3. distillationdistillation under reduced pressure
  4. dissolutionThe residue was dissolved in 10 ml of acetonitrile
  5. washThe methylene chloride layer was washed with water
  6. customdried
  7. customevaporated
  8. dissolutionThe residue was dissolved in a mixture of 5 ml of absolute alcohol and 5 ml of ethyl acetate
  9. additionThe reaction mixture of 0.65 ml of acetyl chloride with 2 ml of absolute alcohol
  10. additionwas added to the obtained solution
  11. waitkept at 0° C. for 18 hours
  12. washwashed with ethyl acetate
  13. customdried

Sources & evidence

ORD record
ord-36d21a3e07a0432ab719dfb5c96ab1d2
Source dataset
uspto-grants-1990_08
Patent number
US04950759

Reaction notes

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