Hydrochloric Acid → HCID 178484724, compound

HRID 16122

Reaction equation

HRID 16122 reaction equation
Cl.Cl.Cl.[Cl:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C@H:20]2[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]2)[CH2:14][CH2:13]1.[CH2:27]([N:29]([CH2:32]C)[CH2:30]C)C.ClC(Cl)([O:37]C(=O)OC(Cl)(Cl)Cl)Cl.Cl>ClCCl>[Cl:4][C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[CH:7][C:6]=1[N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C@H:20]2[CH2:25][CH2:24][C@H:23]([NH:26][C:27]([N:29]([CH3:32])[CH3:30])=[O:37])[CH2:22][CH2:21]2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 178478588HCID 178478588, compound

Product 1

HCID 178484724HCID 178484724, compoundYield 143.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.56 g (1.2 mmol) trans-4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]-ethyl}-cyclohexyl-amine trihydrochloride was suspended in dry dichloromethane (50 ml), triethylamine 0.77 ml, 6 mmol) was added and 0.13 g (0.44 mmol) triphosgene dissolved in dichloromethane was dropped in. After one hour stirring at room temperature dimetilamine hydrochloride (0.49 g, 6 mmol) followed by triethylamine (0.84 ml, 6 mmol) was added and the stirring was continued for 20 hours. The mixture was filtered, the filtrate washed with water, dried and evaporated in vacuo. Recrystallizing the product from methanol gave the title compound (0.27 g, 52%). Melting point: 212-4° C.

Workup

  1. additionwas dropped in
  2. additionwas added
  3. filtrationThe mixture was filtered
  4. washthe filtrate washed with water
  5. customdried
  6. customevaporated in vacuo
  7. customRecrystallizing the product from methanol

Sources & evidence

ORD record
ord-258c082de91b464ba0230efdebd317cf
Source dataset
uspto-grants-2010_06
Patent number
US07737142B2

Linked notes

Loading…