Ammonia → HCID 178491972, compound

HRID 1615864Notes

Reaction equation

HRID 1615864 reaction equation
Cl.Cl.[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:5]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]2)[CH2:15][CH2:14]1.C([N:30]([CH2:33]C)CC)C.ClC(Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl.N>ClCCl>[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:5]=1[N:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]2[CH2:22][CH2:23][C@H:24]([NH:27][C:33]([NH2:30])=[O:38])[CH2:25][CH2:26]2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 94429TriphosgeneHCID 178491971HCID 178491971, compound

Product 1

HCID 178491972HCID 178491972, compoundYield 175.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.38 g (3 mmol) trans-4-{2-[4-(2,3-dichloro-4-methoxy-phenyl)-piperazin-1-yl]-ethyl}-cyclohexyl-amine dihydrochloride was suspended in dry dichloromethane (100 ml), triethylamine 1.72 ml, 12.4 mmol) was added and 0.34 g (1.14 mmol) triphosgene dissolved in dichloromethane was dropped in. After one hour stirring at room temperature ammonia (20% solution in methanol) was added and the stirring was continued for 20 hours. The mixture was evaporated. 20 ml water was added, the precipitate filtered, washed with water, dried. Recrystallizing the product from methanol gave 0.86 g trans-1-{4-[2-[4-(2,3-dichloro-4-methoxy-phenyl)-piperazin-1-yl]-ethyl]-cyclohexyl}-urea melting above 250° C. This product was dissolved in dichloromethane (60 ml), then 10 ml (10 mmol) borontribromid solution (1M in CH2Cl2) was dropped in at 5° C. and the mixture stirred at room temperature for 24 hours. The reaction was monitored by TLC. 4 ml methanol was added and the mixture evaporated. 35 ml saturated NaHCO3 solution was added. The precipitate was filtered, washed with water and dried, recrystallized from methanol giving 0.37 g of title compound, melting at 195-8° C.

Workup

  1. additionwas dropped in
  2. additionwas added
  3. customThe mixture was evaporated
  4. addition20 ml water was added
  5. filtrationthe precipitate filtered
  6. washwashed with water
  7. customdried
  8. customRecrystallizing the product from methanol

Sources & evidence

ORD record
ord-6952943b8fae4bb1ac986e65e2242f8a
Source dataset
uspto-grants-2014_07
Patent number
US08765765B2

Reaction notes

Loading…