Sodium Hydroxide → Quetiapine

HRID 2266953Notes

Reaction equation

HRID 2266953 reaction equation
[CH:1]1[C:6]2[C:7]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27]C(=O)C4C=CC=CC=4)[CH2:18][CH2:17]3)=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[CH:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=[C:7]([N:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][O:24][CH2:25][CH2:26][OH:27])[CH2:18][CH2:17]3)[C:6]=2[CH:1]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11352260HCID 11352260, compound

Product 1

HCID 5002Quetiapine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Benzoic acid 2-[2-(4-dibenzo[b,f][1,4]-thiazepin-11-yl-piperazin-1-yl]-ethoxy]-ethyl ester (1.5 g, 2.97 mmol), ethanol (10 ml) and 50% NaOH (1 ml) were charged into a reaction flask. Then the mixture was stirred at 80° C. for 2 h. The reaction mixture was evaporated in vacuo. Ethyl acetate (20 ml) and saturated NaCl-water (15 ml) were added to the residue. The water phase was separated. To the organic phase was added 1 M HCl (10 ml). To the combined water phase was added 50% NaOH until the pH was 12 and saturated NaCl-water (10 ml). The alkaline water phase was extracted twice with ethyl acetate (10 ml). The combined organic phase was washed with saturated NaCl-water (10 ml), dried with Na2SO4 and evaporated. Yield of quetiapine 0.93 g.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionEthyl acetate (20 ml) and saturated NaCl-water (15 ml) were added to the residue
  3. customThe water phase was separated
  4. additionTo the organic phase was added 1 M HCl (10 ml)
  5. additionTo the combined water phase was added 50% NaOH until the pH was 12 and saturated NaCl-water (10 ml)
  6. extractionThe alkaline water phase was extracted twice with ethyl acetate (10 ml)
  7. washThe combined organic phase was washed with saturated NaCl-water (10 ml)
  8. dry with materialdried with Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-3ba90bc51b0f409e9675f8418ddaa13e
Source dataset
uspto-grants-2010_12
Patent number
US07858777B2

Reaction notes

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