Hexane → HCID 21474126, compound

HRID 128642Notes

Reaction equation

HRID 128642 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH:16]3[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH3:24]CCCCC>C(O)=O.C=O>[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]([CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([CH3:24])[CH2:17]3)[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 14798Sodium HydroxideHCID 21474134HCID 21474134, compound

Product 1

HCID 21474126HCID 21474126, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 712FormaldehydeSolvent

Procedure

Dissolved 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)piperidine (0.75 g, 2.7 mmol)in 1.1 mL of formic acid and 1.5 mL of 37% aqueous formaldehyde. Heated in a 90°-95° C. oil bath for 20 hours. Cooled to room temperature, and made basic with 5% NaOH. Extracted with ether. Dried combined organic extracts with MgSO4, filtered, and evaporated. Crystallized product from hexane to give 0.60 g (76% yield) of 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-l-methyl-piperidine as white solid. Dissolved the free base in ether, and added 19 weight % HCl-EtOH to precipitate the hydrochloride salt.

Workup

  1. temperatureHeated in a 90°-95° C. oil bath for 20 hours
  2. extractionExtracted with ether
  3. customDried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-cbaf44fe25ae4421aa889d5112569218
Source dataset
uspto-grants-1995_11
Patent number
US05464840

Reaction notes

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