Tetrahydrofuran → HCID 53911027, compound

HRID 845431Notes

Reaction equation

HRID 845431 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)(=O)[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O1[CH2:27][CH2:26][CH2:25][CH2:24]1>>[CH:24]1[C:26]2[CH:27]=[CH:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[CH:24]([CH:20]3[CH2:21][CH2:22][N:17]([CH2:7][CH:8]=[CH:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[CH2:18][CH2:19]3)[C:25]=2[CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 223147HCID 223147, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53911027HCID 53911027, compound

Procedure

0.78 gram (20.6 millimoles) of lithium aluminum hydride was added in small portions under argon atmosphere to a solution of the above prepared cinnamoylpiperidine in 50 milliliters of dry tetrahydrofuran to obtain 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-cinnamylpiperidine in the reaction mixture. The latter was recovered in the usual manner, i.e., diluting with tetrahydrofuran, quenching by the "n,n,3n" method, drying the solution over magnesium sulfate, vaporizing the solvent in vacuo from the filtered dried solution thereby obtaining a residue, flash chromatographing the residue on silica gel employing 75/25 ethyl acetate-hexane as eluant to produce 681 grams of a purified 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-cinnamylpiperidine base product. The base was dissolved in methanol and a solution of 219 milligrams (1 equivalent) oxalic acid dihydrate in 2 milliliters of methanol added to the solution of the base and the resulting mixture allowed to stand overnight to obtain 4-(5H-dibenzo[a,d]cyclohepten-5-yl)-1-cinnamylpiperidine hydrogen oxalate product as crystals melting 218°-220° C. The product had elemental analyses as follows:

Sources & evidence

ORD record
ord-b3871ea349a045a997834cb5ca9a9fa7
Source dataset
uspto-grants-1988_07
Patent number
US04758577

Reaction notes

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