Ethanol → HCID 21402927, compound

HRID 972958Notes

Reaction equation

HRID 972958 reaction equation
[CH:1]1[C:11]2[CH2:10][CH:9]([CH2:12][NH2:13])[C:8]3[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=3[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:18]1(=[O:24])[O:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>O>[CH:1]1[C:11]2[CH2:10][CH:9]([CH2:12][NH:13][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][OH:24])[C:8]3[CH:14]=[CH:15][CH:16]=[CH:17][C:7]=3[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10953Delta-ValerolactoneHCID 11430Potassium CarbonateHCID 21402968HCID 21402968, compound

Product 1

HCID 21402927HCID 21402927, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

10,11-Dihydro-5H-dibenzo[a,d]cycloheptene-10-methylamine, γmaxCHCl3 3390, 3300 cm-1, (52.3g, 0.234 mole), is combined with δ-valerolactone (35g, 0.35 mole). The mixture is heated for 2 hr. at 150° C (oil bath temperature). After partial cooling, ethanol (250 ml) is added followed by a solution of potassium carbonate (50 g, 0.36 mole) in water (150 ml). The two-phase mixture is stirred at 60° C overnight. The ethanol is removed under reduced pressure and the residual mixture extracted with chloroform. The chloroform solution is washed with water, dried and taken to dryness. The residue is crystallized from benzene (750 ml) - ether (ca 800 ml) affording N-[(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-yl)methyl]-5-hydroxyvaleramide, m.p. 96°-98° C, γmaxCHCl3 3630, 3445, 3350, 1663 cm-1.

Workup

  1. temperatureThe mixture is heated for 2 hr
  2. customat 150° C
  3. customThe ethanol is removed under reduced pressure
  4. extractionthe residual mixture extracted with chloroform
  5. washThe chloroform solution is washed with water
  6. customdried
  7. customThe residue is crystallized from benzene (750 ml) - ether (ca 800 ml)

Sources & evidence

ORD record
ord-fe7c57275cd7434a917f207cfb9a11bd
Source dataset
uspto-grants-1977_10
Patent number
US04054569

Reaction notes

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