Ammonia → HCID 54346393, compound

HRID 1704661Notes

Reaction equation

HRID 1704661 reaction equation
O[C:2]1([CH2:14][CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]([CH3:13])[CH2:5][CH2:4][CH2:3]1.C(OCC)C.N.[Li]>C(O)C>[CH2:18]([N:17]([CH2:16][CH2:15][CH2:14][CH:2]1[C:8]2[CH2:9][CH:10]=[CH:11][CH2:12][C:7]=2[CH:6]([CH3:13])[CH2:5][CH2:4][CH2:3]1)[CH2:20][CH3:21])[CH3:19]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 3028194LithiumHCID 54036827HCID 54036827, compound

Product 1

HCID 54346393HCID 54346393, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 5-hydroxy-5-diethylaminopropyl-9-methyl-6,7,8,9-tetrahydro-5H-benzocycloheptene is dissolved in 100 ml. of diethyl ether and added to 500 ml. of liquid ammonia. The solution is treated with 20 g. of lithium in small portions. After 1/2 hr., the mixture is treated slowly dropwise with absolute ethanol until the color discharges completely. After removal of NH3, the residue is cooled, treated with water and extracted with ether. The dried extracts are freed of solvent leaving crude 5-diethylaminopropyl-9-methyl-1,4,6,7,8,9-hexahydro-5H-benzocycloheptene, which is converted to the corresponding tetrol as described hereinbefore.

Workup

  1. additionThe solution is treated with 20 g
  2. customAfter removal of NH3
  3. temperaturethe residue is cooled
  4. additiontreated with water
  5. extractionextracted with ether

Sources & evidence

ORD record
ord-260b2051ae9143d69e5161ad81944c0c
Source dataset
uspto-grants-1978_11
Patent number
US04127578

Reaction notes

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