Triethylamine → HCID 69677717, compound

HRID 584180Notes

Reaction equation

HRID 584180 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:39]=[C:40]([Cl:42])[CH:41]=1)[C:36](Cl)=[O:37]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:36](=[O:37])[C:35]2[CH:34]=[C:33]([Cl:32])[CH:41]=[C:40]([Cl:42])[CH:39]=2)[C@H:10]([CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 761913,5-Dichlorobenzoyl chlorideHCID 54384374HCID 54384374, compound

Product 1

HCID 69677717HCID 69677717, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3R)-1-benzyl-3-(2-naphthylmethyl)piperazine (3.23 g) and triethylamine (4.3 ml) in dichloromethane (60 ml) was added a solution of 3,5-dichlorobenzoyl chloride (6.0 g) in dichloromethane (10 ml) at 0° C. After stirring at room temperature for 3 hours, the mixture was quenched with water and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, and evaporated under reduced pressure. The obtained residue was triturated with a mixture of dichloromethane and hexane to give (2R)-4-benzyl-1-(3,5-dichlorobenzoyl)-2-(2-naphthylmethyl)piperazine.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe obtained residue was triturated with a mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-e69d729771854ae788b23600b0ad806a
Source dataset
uspto-grants-2005_08
Patent number
US06924278B2

Reaction notes

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