Methylamine → HCID 178485941, compound

HRID 1615863Notes

Reaction equation

HRID 1615863 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.[CH2:28]([N:30]([CH2:33]C)CC)C.ClC(Cl)([O:38]C(=O)OC(Cl)(Cl)Cl)Cl.CN>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:28]([NH:30][CH3:33])=[O:38])[CH2:25][CH2:26]2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 178491971HCID 178491971, compound

Product 1

HCID 178485941HCID 178485941, compoundYield 170.1%

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 methylamine (33% solution in ethanol) 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 trans-1-{4-[2-[4-(2,3-dichloro-4-methoxy-phenyl)-piperazin-1-yl]-ethyl]-cyclohexyl}-3-methyl-urea (0.86 g, 65%) 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 0.34 g of title compound, melting at 237-41° 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-1fe55111a0f949f994cf9732bf2e9ebf
Source dataset
uspto-grants-2014_07
Patent number
US08765765B2

Reaction notes

Loading…