Lithium hydroxide, monohydrate → HCID 18963970, compound

HRID 257057Notes

Reaction equation

HRID 257057 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH2:22][CH2:23][N:24]([O:28]C(=O)C)[C:25](=[O:27])[CH3:26])[CH:17]=3)[C:12]2=[O:32])=[CH:4][CH:3]=1.O.[OH-].[Li+]>C(O)(C)C.O.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH2:22][CH2:23][N:24]([OH:28])[C:25](=[O:27])[CH3:26])[CH:17]=3)[C:12]2=[O:32])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 18963901HCID 18963901, compound

Product 1

HCID 18963970HCID 18963970, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21889133Propan-2-ol--water (1/1)Solvent

Procedure

2-[3-(4-Fluorophenyl)-propyl]-6-[2-(N-acetyloxy-N-acetylamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline (2.0 g) is dissolved in 40 ml of an isopropanol/water mixture (1:1) and treated with 0.94 g (25 mmol) of lithium hydroxide monohydrate for 30 minutes at room temperature. The mixture is diluted with ether and the organic phase is removed. The aqueous layer is brought to pH of approximately 3 with 2N HCl, and extracted with ether. The combined acidic extracts are dried (MgSO4) and evaporated to dryness to yield 2-[3-(4-fluorophenyl)-propyl]-6-[2-(N-hydroxy-N-acetylamino)-ethoxy]-1-oxo-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. customthe organic phase is removed
  2. extractionextracted with ether
  3. dry with materialThe combined acidic extracts are dried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-2d4dd33527cc4644b3cdfa8f36d968e9
Source dataset
uspto-grants-1993_11
Patent number
US05260316

Reaction notes

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