Dimethylcarbamoyl Chloride → HCID 178484723, compound

HRID 645464Notes

Reaction equation

HRID 645464 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.C(N(CC)CC)C.[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>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:36]([N:35]([CH3:39])[CH3:34])=[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

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178478717HCID 178478717, compound

Product 1

HCID 178484723HCID 178484723, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.4 g (1 mmol) trans-4-{2-[4-(indan-4-yl)-piperazin-1-yl]-ethyl}-cyclohexyl-amine dihydrochloride was suspended in dichloromethane (30 ml), triethylamine (0.56 ml, 4 mmol) was added followed by 0.12 ml (1.3 mmol) N,N-dimethylcarbamoylchloride. The reaction mixture was stirred for 24 hours at room temperature. 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 (0.2 g, 50%), melting at 150-2° C.

Workup

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

Sources & evidence

ORD record
ord-3fde0f2c8f2c4baaa672c33bdb84eeb8
Source dataset
uspto-grants-2010_04
Patent number
US07705003B2

Reaction notes

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