Water → HCID 13019460, compound

HRID 2285729Notes

Reaction equation

HRID 2285729 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH2:10][CH2:11][CH:12]([C:18]1[CH:27]=[CH:26][C:21]([C:22](OC)=[O:23])=[CH:20][CH:19]=1)[C:13]1[NH:14][CH:15]=[CH:16][N:17]=1)[CH3:9].O.C(O)(=O)/C=C\C(O)=O>O1CCCC1.CO>[CH3:7][N:8]([CH2:10][CH2:11][CH:12]([C:18]1[CH:19]=[CH:20][C:21]([CH2:22][OH:23])=[CH:26][CH:27]=1)[C:13]1[NH:17][CH:16]=[CH:15][N:14]=1)[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 444266Maleic AcidHCID 13019466HCID 13019466, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13019460HCID 13019460, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.4 g) was added slowly to a stirred solution of 4-[3-(N,N-dimethylamino)-1-(imidazol-2-yl)propyl]benzoic acid, methyl ester (1.0 g) in dry tetrahydrofuran (40 ml) under nitrogen. After stirring for 2 hr., water (3 ml) was added, and the granular suspension was filtered off. The filtrate was evaporated to dryness to give a colourless gum which was dissolved in methanol (5 ml) and treated with a solution of maleic acid (0.4 g) in methanol (5 ml). Solvent was removed and the residual gum was triturated with dry ether to give the maleate salt hemihydrate of the title compound as a glassy, hygroscopic solid, m.p. 65°-66° (1.1 g); τ(D2O)2.4-2.65(4H,m,aromatic),2.70(2H,s,imidazole),5.33, ##STR35## 6.7-7.6(10H,m,CH2CH2N(CH3)2),7.08 (6H,s,N(CH3)2).

Workup

  1. filtrationthe granular suspension was filtered off
  2. customThe filtrate was evaporated to dryness
  3. customto give a colourless gum which
  4. customSolvent was removed
  5. customthe residual gum was triturated with dry ether

Sources & evidence

ORD record
ord-a1909a3d42734572b8349d720ea2b295
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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