Triethylamine → 3-[3-Chloro-2'-(4-methyl-piperazine-1-carbonyl)-biphenyl-4-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

HRID 415995Notes

Reaction equation

HRID 415995 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[C:22]([C:27](O)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[C:10]1=[O:20].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:58][N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1>CN(C=O)C.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:27]([N:62]2[CH2:63][CH2:64][N:59]([CH3:58])[CH2:60][CH2:61]2)=[O:28])[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[C:10]1=[O:20]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 59299474HCID 59299474, compound

Product 1

HCID 666216203-[3-Chloro-2'-(4-methyl-piperazine-1-carbonyl)-biphenyl-4-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride saltYield 126.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Charge a vial with 3′-chloro-4′-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-biphenyl-2-carboxylic acid (70 mg, 0.17 mmol), EDCI (65 mg, 0.34 mmol) and HOBt (23 mg, 0.17 mmol). Dissolve in DMF (0.1 M) and add triethylamine (95 μL, 0.68 mmol) and N-methyl piperazine (34 mg, 0.34 mmol). Stir at room temperature overnight. Pour into water and extract with ether. Dry over sodium sulfate, filter and concentrate. Purify over silica gel. Dissolve the residue in methylene chloride and acidify with 4N HCl in dioxane. Concentrate in vacuo which affords 57 mg (63%) of the title compound: Mass spectrum m/z=494.3 (M+H−HCl).

Workup

  1. extractionextract with ether
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify over silica gel
  6. dissolutionDissolve the residue in methylene chloride
  7. concentrationConcentrate in vacuo which

Sources & evidence

ORD record
ord-e8d112c00a9b45f1acd6fe234a58825e
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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