Ammonia → 1-[2-(4-Chlorophenyl)ethyl]piperazine

HRID 1769005

Reaction equation

HRID 1769005 reaction equation
C(OCCN(C1C=CC(C([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[CH2:20][CH2:19]2)=O)=CC=1)C(=O)CCl)(C)C.Cl.N.N[C@H](C(NCC(O)=O)=O)CS>C(Cl)Cl>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][N:21]2[CH2:20][CH2:19][NH:18][CH2:23][CH2:22]2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 439498L-CysteinylglycineHCID 98073911-{4-[N-(2-isopropyloxyethyl)-N-chloroacetylamino]benzoyl}-4-[2-(4-chlorophenyl)ethyl]piperazine

Product 1

HCID 122357141-[2-(4-Chlorophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Analogously to Example 1, 1.6 g of 1-{4-[N-(2-isopropoxyethyl)-N-chloroacetyl-amino]-benzoyl}-4-[2-(4-chlorophenyl)-ethyl]-piperazine--freed from the corresponding hydrochloride by treatment with a mixture of aqueous ammonia solution/methylene chloride--are reacted with 0.55 g of L-cysteinyl-glycine, yielding 1-{{4-{N-2-isopropoxyethyl)-N-[[[2R]-2-[N'-(carboxymethyl)carbamoyl]-2-amino-ethylmercapto-acetyl]]-amino}-benzoyl}}-4-[2-(4-chlorophenyl)-ethyl]-piperazine. The hemihydrate thereof has a melting point of 85°-87° and an αD25 =-1.5° (c=0.545%, methanol).

Sources & evidence

ORD record
ord-7502e364967e4e01878d20fed8cab89f
Source dataset
uspto-grants-1995_01
Patent number
US05380726

Linked notes

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