Water → HCID 68120121, compound

HRID 1284232Notes

Reaction equation

HRID 1284232 reaction equation
[C:1]([NH:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[CH:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2)(=[O:5])[CH2:2][CH2:3][CH3:4].CC[O:27][CH2:28][CH3:29].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-:36].[Na+].[OH2:38]>>[C:28]([OH:27])(=[O:38])/[CH:29]=[CH:2]\[C:1]([OH:5])=[O:36].[CH2:1]([NH:6][CH2:7][CH2:8][CH2:9][CH:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[CH:13][C:12]2[CH:21]=[CH:22][CH:23]=[CH:24][C:11]1=2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 5

HCID 962Water2×HCID 3283Diethyl Ether2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21412107HCID 21412107, compound

Product 1

HCID 68120121HCID 68120121, compound

Procedure

In a system protected by a drying tube and in which a nitrogen atmosphere is maintained, a solution of the product from Step A. (0.80 g., 0.0075 mole) in 25 ml. of absolute ether is added dropwise to a stirred suspension of lithium aluminum hydride (0.19 g., 0.0025 mole) in 15 ml. of absolute ether. After stirring at reflux for 1 hour, the mixture is cooled in ice and hydrolyzed by the successive dropwise addition of water, 0.2 ml., 20% sodium hydroxide, 0.2 ml., and water, 0.6 ml. The granular precipitate is collected and washed thoroughly with ether. The combined ethereal filtrate and washings are washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness. The residual oily base is dissolved in absolute ether and treated with a solution of maleic acid (10% excess) in absolute alcohol. The 5-(3-n-butylaminopropyl)-5H-dibenzo[a,d]cycloheptene hydrogen maleate is obtained by dilution of the solution with absolute ether as white needles, m.p. 102°-107°C., in a yield of 0.65 g. (60%). Recrystallization from mixtures of isopropyl alcohol - absolute ether and absolute alcohol - absolute ether gives product, m.p. 107.5°-109°C.

Workup

  1. customIn a system protected by a drying tube and in which
  2. temperaturea nitrogen atmosphere is maintained
  3. temperatureat reflux for 1 hour
  4. customThe granular precipitate is collected
  5. washwashed thoroughly with ether
  6. washThe combined ethereal filtrate and washings are washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness
  9. dissolutionThe residual oily base is dissolved in absolute ether
  10. additiontreated with a solution of maleic acid (10% excess) in absolute alcohol

Sources & evidence

ORD record
ord-df20a081bda94113949ce8b75c767994
Source dataset
uspto-grants-1976_08
Patent number
US03978121

Reaction notes

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