Potassium Hydroxide → HCID 12694108, compound

HRID 647544Notes

Reaction equation

HRID 647544 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[S:30][C:15]3([CH2:20][CH2:19][N:18](C(OC4C=CC=CC=4)=O)[CH2:17][CH2:16]3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=3)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37]>C(O)CO.CCOCC>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]\[C:36]([OH:38])=[O:37].[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[S:30][C:15]3([CH2:16][CH2:17][NH:18][CH2:19][CH2:20]3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=3)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 444266Maleic AcidHCID 12694090HCID 12694090, compound

Product 1

HCID 12694108HCID 12694108, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
160 °C

Procedure

To 6.97 g of 3-(3-fluorophenyl)-1,3-dihydro-1'-phenoxycarbonylspiro[benzo(c)thiophene-1,4'-piperidine] of Example 57 in 100 ml of ethylene glycol, under nitrogen, at 150° C. is added 16 g of 85% potassium hydroxide pellets. The reaction is stirred in a 160° C. bath for 45 minutes. The solution is then poured into 225 ml of ice-water, diluted to 500 ml and extracted with three 175 ml portions of dichloromethane. The combined dichloromethane extracts are washed with 200 ml portions of water and one 50 ml portion of saturated aqueous sodium chloride solution, and dried over magnesium sulfate to give a solid free base. The free base in ether is treated with ethereal maleic acid to give a salt. The salt is washed with ether and recrystallized from methanol-acetone-ether to give a white powder of 3-(3-fluorophenyl)-1,3-dihydrospiro[benzo(c)thiophene-1,4'-piperidine] maleate, m.p. 188°-188.5° C.

Workup

  1. additiondiluted to 500 ml
  2. extractionextracted with three 175 ml portions of dichloromethane
  3. washThe combined dichloromethane extracts are washed with 200 ml portions of water and one 50 ml portion of saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customto give a solid free base
  6. customto give a salt
  7. washThe salt is washed with ether
  8. customrecrystallized from methanol-acetone-ether

Sources & evidence

ORD record
ord-5cb7b7755b8c46fb85681e24f18f8ec8
Source dataset
uspto-grants-1983_10
Patent number
US04409229

Reaction notes

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