Acetic Acid → HCID 18700219, compound

HRID 356626Notes

Reaction equation

HRID 356626 reaction equation
[N:1]1([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:26]=[CH:25]3)[CH2:21][CH2:20]2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)[CH2:3][CH2:2]1.C(O)(=O)C>C(O)C.[Pd]>[N:1]1([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]3([C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25]3)[CH2:21][CH2:20]2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 131720119HCID 131720119, compound2×

Product 1

HCID 18700219HCID 18700219, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1,4-Bis-spiro[ind-2-en-1,4'-piperidin-1'-yl]butane (compound 4a) (3 g) in ethanol (90 ml) were added acetic acid (5 ml) and 5% palladium on carbon (0.9 g). The mixture was hydrogenated in a Parr apparatus for 2 hours ar 3 atm. The catalyst was filtered off and the solvent evaporated. The remaining oil was dissolved in diluted aqueous NH4OH (200 ml, pH>9). The title compound 5a was extracted with ethyl acetate and worked-up as above and finally crystallized from ethyl acetate. Yield 1.6 g. Mp 113°-115° C. 1H NMR (CDCl3) δ 1.55-1.65 (m, 8 H). 1.95-2.10 (m, 8 H), 2.15 (t, 4 H), 2.45 (broad s, 4 H), 2.95 (t, 8 H), 7.10-7.30 (m, 8 H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. dissolutionThe remaining oil was dissolved in diluted aqueous NH4OH (200 ml, pH>9)
  4. extractionThe title compound 5a was extracted with ethyl acetate
  5. customfinally crystallized from ethyl acetate

Sources & evidence

ORD record
ord-6b72fbb439954e918a6fc7be2a495ad3
Source dataset
uspto-grants-1998_11
Patent number
US05837707

Reaction notes

Loading…