Sodium Hydroxide → HCID 9869513, compound

HRID 1602854Notes

Reaction equation

HRID 1602854 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]([C:20]2[CH:21]=[C:22]([NH:26][C:27]([N:29]3[CH2:38][CH2:37][C:32]4(OCC[O:33]4)[CH2:31][CH2:30]3)=[O:28])[CH:23]=[CH:24][CH:25]=2)([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[OH-].[Na+]>Cl>[O:33]=[C:32]1[CH2:37][CH2:38][N:29]([C:27]([NH:26][C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([C:5]3([N:8]4[CH2:13][CH2:12][N:11]([C:14]5[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH2:10][CH2:9]4)[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:7][CH2:6]3)[CH:21]=2)=[O:28])[CH2:30][CH2:31]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15886820HCID 15886820, compound

Product 1

HCID 9869513HCID 9869513, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-[3-[4-methyl-1-(4-phenyl-1-piperazinyl)-cyclohexyl]phenyl]-1,4-dioxa-8-azaspiro[4.5]decane-8-carboxamide (cis isomer) (34 mg, 0.066 mmol) was dissolved in 4 mL of 6N HCl and the clear homogeneous solution was allowed to stand for 1 h at room temperature. The reaction mixture was made basic with 1N NaOH, extracted with CH2Cl2, dried (Na2SO4) and concentrated to give the crude ketone. The residue was triturated with 30% EtOAc/hexanes to yield colorless crystals of 4-(oxo)-N-[3-[4-methyl-1-(4-phenyl-1-pipera-zinyl)-cyclohexyl]phenyl]-1-piperidinecarboxamide (cis isomer). mp=~173° C. (decomp.).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give the crude ketone
  5. customThe residue was triturated with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-4c1003c315a04b12908d482b39ea9d4d
Source dataset
uspto-grants-1999_11
Patent number
US05985873

Reaction notes

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