HCID 131719610, compound → HCID 131719609, compound

HRID 864848Notes

Reaction equation

[ClH:1].Cl.[N:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][N:10]2[CH2:15][CH2:16][CH2:17][C:18]([O:20]CC)=[O:19])=[CH:5][CH:4]=1>Cl>[ClH:1].[ClH:1].[N:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][N:10]2[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the product of step (i) (5 g) and conc. HCl (50 ml) was heated at 100° C. for 45 min. The resultant solution was evaporated to dryness and the residue dissolved again in conc. HCl and heated to 100° C. for a further 45 min. The reaction mixture was evaporated to dryness, and the residue was twice triturated with toluene, and evaporated to dryness, collected and washed with ether. The crude product was crystallised from hot methanol/ether to give 4-[(4-pyridyl)piperazin-1-yl]butyric acid, dihydrochloride as an off-white crystalline solid (3.45 g): m.p. 280°-300° C. (dec); NMR (d6 -DMSO) δ2.00 (2H, m), 2.36 (2H, t), 3.12 (2H, m), 3.00-3.70 (4H, v. br, m), 3.50-4.50 (4H, v. br, m), 7.30 (2H, d), 8.35 (2H, d), 12.2 (1H, v. br); m/Z 250 (M+H)+ ; calculated for C13H19N3O2. 2.0 HCl. 0.5 H2O: C, 47.1%; H, 6.69%; N, 12.7%; found: C, 47.5%; H, 6.7%; N, 12.5%

Workup

customThe resultant solution was evaporated to dryness
dissolutionthe residue dissolved again in conc. HCl
temperatureheated to 100° C. for a further 45 min
customThe reaction mixture was evaporated to dryness
customthe residue was twice triturated with toluene
customevaporated to dryness
customcollected
washwashed with ether
customThe crude product was crystallised from hot methanol/ether

Sources & evidence

ORD record: ord-575970f325374b46bc99e05a7eac8b1d
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05563141

Reaction notes

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