Ammonia → HCID 20232498, compound

HRID 2290459Notes

Reaction equation

HRID 2290459 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](Cl)=[O:35])=[CH:29][CH:28]=1.N>C(Cl)Cl>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([N:4]2[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][C:9]3[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=3)[CH2:2][CH2:3]2)=[O:35])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1049PyridineHCID 906924-Chlorophenylacetyl chlorideHCID 20232457Ethyl 4-[2-(1-piperazinyl)ethyl]benzoate

Product 1

HCID 20232498HCID 20232498, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a mixture of 9.7 g. (37 mmole) ethyl 4-[2-(piperazin-1-yl)-ethyl]-benzoate, 40 ml. methylene chloride and 6.3 g. (80 mmole) anhydrous pyridine is added dropwise at 0° C., in the course of 40 minutes, a solution of 7.0 g. (37 mmole) 4-chlorophenylacetyl chloride in 20 ml. methylene chloride, a cheesy precipitate being formed. After stirring at 20° C. for 4 hours, the reaction mixture is poured into 250 ml. ice water, rendered alkaline with ammonia and extracted several times with methylene chloride. The methylene chloride solution is washed twice with water, dried with anhydrous sodium sulphate and evaporated. After the addition of ligroin, crystallisation occurs. The product is recrystallised from diethyl ether to give 51% of theory of the desired product; m.p. 88°-89° C.

Workup

  1. additionTo a mixture of 9.7 g
  2. additionthe reaction mixture is poured into 250 ml
  3. extractionextracted several times with methylene chloride
  4. washThe methylene chloride solution is washed twice with water
  5. dry with materialdried with anhydrous sodium sulphate
  6. customevaporated
  7. additionAfter the addition of ligroin, crystallisation
  8. customThe product is recrystallised from diethyl ether

Sources & evidence

ORD record
ord-fa854587686541a89e4bc48396f63227
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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