Acetic Anhydride → HCID 178478895, compound

HRID 1253261Notes

Reaction equation

HRID 1253261 reaction equation
[CH:1]1([C:9]([OH:11])=[O:10])[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.C(OC(=O)C)(=O)C.[ClH:19].[NH2:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][N:28]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:27][CH2:26]1.C(N(CC)CC)C>O.C1(C)C(C)=CC=CC=1>[ClH:19].[ClH:19].[CH2:31]([N:28]1[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][CH2:22][CH2:21][N:20]=[C:6]([CH:3]2[CH2:4][CH2:5][CH:1]([C:9]([OH:11])=[O:10])[CH2:2]2)[OH:8])[CH2:30][CH2:29]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 1072161,3-Cyclopentanedicarboxylic acidHCID 201374991-(4-Aminobutyl)-4-benzylpiperazine hydrochloride

Product 1

HCID 178478895HCID 178478895, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

1,3-Cyclopentane dicarboxylic acid (8.0 g., 51 mmole) was converted to the anhydride by refluxing for 3 hours in 100 ml. of acetic anhydride. The excess solvent was removed under vacuum and the residue was stored in vacuum for 18 hours. The crude anhydride thus obtained was combined with 14 g. (50 mmole) of 1-(4-aminobutyl)-4-benzylpiperazine hydrochloride and 5.0 g. (50 mmole) of triethylamine in 500 ml. of xylene. The mixture was refluxed for 48 hours with water separation via a Dean-Stark trap. The product was concentrated under vacuum and chromatographed on 200 g. of silica gel with 2% ethanol/chloroform. The product was crystallized from ethanol by addition of 4N HCl/isopropyl alcohol to obtain cyclopentane-1,3-dicarboxylic-N-[4-(4-benzyl-1-piperazinyl)butyl]imide dihydrochloride; m.p. 273°-275° C.

Workup

  1. temperatureby refluxing for 3 hours in 100 ml
  2. customThe excess solvent was removed under vacuum
  3. customThe crude anhydride thus obtained
  4. concentrationThe product was concentrated under vacuum
  5. customchromatographed on 200 g
  6. customThe product was crystallized from ethanol by addition of 4N HCl/isopropyl alcohol

Sources & evidence

ORD record
ord-08521a6b0d0b4fd3934f670411b3b9a9
Source dataset
uspto-grants-1988_05
Patent number
US04748240

Reaction notes

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