1-Propanol → 147900-42-3

HRID 258199Notes

Reaction equation

HRID 258199 reaction equation
[ClH:1].[NH2:2][CH:3]([CH:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[CH:12][C:11]2[CH:20]=[CH:21][CH:22]=[CH:23][C:10]1=2)[C:4]([O:6]CC)=[O:5].[OH-].[K+].CCCCCC.C(O)CC>C(O)C.O>[ClH:1].[NH2:2][CH:3]([CH:9]1[C:10]2[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=2[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2)[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 10311-PropanolHCID 8058HexaneHCID 14797Potassium HydroxideHCID 131718256HCID 131718256, compound

Product 1

HCID 9861189147900-42-3

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl α-amino-5H-dibenzo[a,d]cycloheptene-5-acetate, hydrochloride (0.21 g, 0.6 mmol) dissolved in 10 mL of absolute ethanol is stirred with 3 mL of 1.25 M ethanolic potassium hydroxide solution until TLC (SiO2, hexane:2 propanol/3:1) shows no starting material (2 hours). The solvent is stripped and a residual solid is taken up in water and extracted with dichloromethane. The aqueous layer is acidified with 6 N hydrochloric acid to pH 1 and stripped to dryness. The residue is treated with 5 mL of boiling water, cooled to room temperature, then refrigerated overnight. A solid is collected, washed with diethyl ether (0.05 g); mp 225° C. (dec).

Workup

  1. customno starting material (2 hours)
  2. extractionextracted with dichloromethane
  3. additionThe residue is treated with 5 mL of boiling water
  4. customrefrigerated overnight
  5. customA solid is collected
  6. washwashed with diethyl ether (0.05 g)

Sources & evidence

ORD record
ord-c795d1c7186342df8c584e7151c5d4c8
Source dataset
uspto-grants-1993_11
Patent number
US05264577

Reaction notes

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