Sulfuric acid magnesium salt (1:1) → HCID 20330260, compound

HRID 2057760Notes

Reaction equation

HRID 2057760 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([C:19](OCC)=[O:20])[CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl-].[NH4+].S([O-])([O-])(=O)=O.[Mg+2]>CCOCC>[CH3:1][N:2]1[CH2:3][CH2:4][C:5](=[C:8]2[C:14]3[CH:15]=[C:16]([CH2:19][OH:20])[CH:17]=[CH:18][C:13]=3[CH2:12][CH2:11][C:10]3[CH:24]=[CH:25][CH:26]=[CH:27][C:9]2=3)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517Ammonium ChlorideHCID 12834405HCID 12834405, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20330260HCID 20330260, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 5.3 g of the ethyl ester from Step A in 200 ml of ether was added dropwise over about 30 minutes to a stirred mixture of 0.53 g of LiAlH4 and 50 ml of ether. After the addition was complete the mixture was stirred 1 hour at ambient temperature, warmed to reflux and allowed to cool spontaneously to ambient temperature. With vigorous stirring a saturated aqueous solution of ammonium chloride was added slowly until a granular precipitate and a clear ether phase formed. Anhydrous magnesium sulfate was added. After stirring a short time the mixture was filtered and the filtrate was concentrated to dryness to give 2.28 g of 1-methyl-4-(10,11-dihydro-3-hydroxymethyl-5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidine, m.p. 178°-181° C. after recrystallization from acetonitrile.

Workup

  1. additionAfter the addition
  2. temperaturewarmed
  3. temperatureto reflux
  4. temperatureto cool spontaneously to ambient temperature
  5. additionwas added slowly until a granular precipitate
  6. stirringAfter stirring a short time the mixture
  7. filtrationwas filtered
  8. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-448436fef5144f5a827ca8c0f0fbfbd6
Source dataset
uspto-grants-1980_07
Patent number
US04212871

Reaction notes

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