tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-(2-(3,3-bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetyl)piperazine-1-carboxylate

HRID 2408854Notes

Reaction equation

HRID 2408854 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14](O)=[O:15])[C:9]2=[O:17])=[CH:4][CH:3]=1.[N:25]1([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14]([N:28]3[CH2:27][CH2:26][N:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:30][CH2:29]3)=[O:15])[C:9]2=[O:17])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673873472-(3,3-Bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetic acid

Product 1

HCID 86657628tert-Butyl 4-(2-(3,3-bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 25D (0.8 g, 2.2 mmol) in CH2Cl2 (30 mL) was added tert-butyl piperazine-1-carboxylate (0.41 g, 2.2 mmol) under nitrogen. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.84 g, 4.4 mmol) and 4-(dimethylamino)pyridine (0.027 g, 0.22 mmol) were added, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was then washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; (CH3OH/CH2Cl2, 2:98 eluant) to afford the title compound.

Workup

  1. washThe reaction mixture was then washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel (Analogix Intelliflash 280

Sources & evidence

ORD record
ord-aa43a0dc2ae9417f8d79906d9e984c55
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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