Diethylamine → HCID 178464323, compound

HRID 645466Notes

Reaction equation

HRID 645466 reaction equation
Cl.Cl.[CH2:3]1[C:11]2[C:6](=[C:7]([N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C@H:20]4[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22][CH2:21]4)[CH2:14][CH2:13]3)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[CH2:27]([N:29]([CH2:32][CH3:33])[CH2:30]C)[CH3:28].ClC(Cl)([O:37]C(=O)OC(Cl)(Cl)Cl)Cl.C(NCC)C>ClCCl>[CH2:3]1[C:11]2[C:6](=[C:7]([N:12]3[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C@H:20]4[CH2:21][CH2:22][C@H:23]([NH:26][C:30]([N:29]([CH2:32][CH3:33])[CH2:27][CH3:28])=[O:37])[CH2:24][CH2:25]4)[CH2:16][CH2:17]3)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 178478717HCID 178478717, compound

Product 1

HCID 178464323HCID 178464323, compoundYield 146.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.48 g (1.2 mmol) trans-4-{2-[4-(indan-4-yl)-piperazin-1-yl]-ethyl}-cyclohexyl-amine dihydrochloride was suspended in dry dichloromethane (50 ml), triethylamine 0.67 ml, 4.8 mmol) was added and 0.14 g (0.48 mmol) triphosgene dissolved in dichloromethane was dropped in. After one hour stirring at room temperature diethylamine (0.62 ml, 6 mmol) was added and the stirring was continued for 20 hours. The solution was extracted with water (2×8 ml), dried and evaporated in vacuo. The residue was purified using flash chromatography giving the title compound (0.3 g, 58%), melting point: 157-9° C.

Workup

  1. additionwas dropped in
  2. additionwas added
  3. extractionThe solution was extracted with water (2×8 ml)
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-1201c965ce9040b9b725feab725a1bea
Source dataset
uspto-grants-2010_04
Patent number
US07705003B2

Reaction notes

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