Hydrochloric Acid → HCID 18931130, compound

HRID 1598997Notes

Reaction equation

HRID 1598997 reaction equation
[C:1]([NH:5][CH2:6][C:7]1([OH:20])[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22].Cl>C1COCC1>[CH2:13]([N:10]1[CH2:11][CH2:12][C:7]2([O:20][C:21](=[O:22])[N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:6]2)[CH2:8][CH2:9]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 54150474HCID 54150474, compound

Product 1

HCID 18931130HCID 18931130, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (tert-butyl)(1-benzyl-4-hydroxypiperidin-4-ylmethyl)amine (11.9 g, 43 mmol), 1,1'-carbonyldiimidazole (8.4 g, 52 mmol) and THF (150 mL) was heated 3.5 hours at reflux. The mixture was cooled, poured into dilute hydrochloric acid and then washed with methylene chloride (2× 200 mL). The combined washes were extracted with dilute hydrochloric acid and the combined. aqueous layers were treated with sodium hydroxide and extracted with methylene chloride. The extract was dried (Na2 SO4) and concentrated and the residue was recrystallized from heptane to give 8-benzyl-3-tert-butyl-3,8-diaza-1-oxaspiro[4.5]decane-2-one (9.98 g, 33 mmol), m.p. 110°-112° C.

Workup

  1. temperaturewas heated 3.5 hours
  2. temperatureat reflux
  3. temperatureThe mixture was cooled
  4. washwashed with methylene chloride (2× 200 mL)
  5. extractionThe combined washes were extracted with dilute hydrochloric acid
  6. additionaqueous layers were treated with sodium hydroxide
  7. extractionextracted with methylene chloride
  8. customThe extract was dried (Na2 SO4)
  9. concentrationconcentrated
  10. customthe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-04e4bc8c0a514540a260fe47126bd6a7
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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