1-Benzylpiperazine → HCID 131716667, compound

HRID 893643Notes

Reaction equation

HRID 893643 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[CH2:10][CH:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]2[N:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:6]12)=[O:4].CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[CH2:45]([N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CCOCC>[ClH:1].[ClH:1].[C:46]1([CH2:45][N:52]2[CH2:53][CH2:54][N:55]([CH2:2][C:3]([N:5]3[CH2:10][CH:9]=[C:8]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=4)[N:7]4[N:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:6]34)=[O:4])[CH2:56][CH2:57]2)[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1

Participants

5

Reactant 3

HCID 759941-BenzylpiperazineHCID 88675Proton sponge2×HCID 15101088HCID 15101088, compound

Product 1

HCID 131716667HCID 131716667, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.065 g of 4-(chloroacetyl)4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, ethyl ester, 535 mg of [1,8-bis(dimethylamino)naphthalene, N,N,N',N'-tetramethyl-1,8-naphthalenediamine],2.88 g of N-benzylpiperazine and 100 ml of dry ether was stirred at room temperature overnight and then filtered. The filtrate was evaporated, the residue dissolved in 300 ml of ether and 1 ml of concentrated hydrochloric acid in 50 ml of water was added. The solid was collected, giving 845 mg of the desired product, mp 228°-230° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. dissolutionthe residue dissolved in 300 ml of ether
  4. addition1 ml of concentrated hydrochloric acid in 50 ml of water was added
  5. customThe solid was collected

Sources & evidence

ORD record
ord-fd862937b2624744bce39498c831f5af
Source dataset
uspto-grants-1992_06
Patent number
US05126340

Reaction notes

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