Ammonia → HCID 54346393, compound

HRID 1287278Notes

Reaction equation

HRID 1287278 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 is small portions. After one-half 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 the residue
  3. temperatureis cooled
  4. additiontreated with water
  5. extractionextracted with ether

Sources & evidence

ORD record
ord-3de916f3e2aa482490687cc9290d49ed
Source dataset
uspto-grants-1976_10
Patent number
US03984407

Reaction notes

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