Ammonia → HCID 21764421, compound

HRID 2287117Notes

Reaction equation

HRID 2287117 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N.[Li].Cl.Cl[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].[Cl-].[NH4+]>CCOCC>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH2:4][CH:3]=[CH:2]1

Participants

7

Reactant 5

HCID 222Ammonia2×HCID 7095BiphenylHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 21764421HCID 21764421, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

23.1 g. of biphenyl in 200 ml. of ether are added to 300 ml. of condensed, dry ammonia and then 2.1 g. of lithium wire (about 2 cm long pieces, de-greased with cyclohexane) are subsequently added at -40° C. over a period of 15 minutes. The mixture is then held at boiling temperature (about -33° C.) for 2 hours. Subsequently, 7.2 g. of 2-chloro-N,N-dimethylethylamine hydrochloride are rapidly added portionwise at about -70° C. The mixture is again warmed to boiling temperature and held at this temperature for 0.5 hour. After the subsequent addition of ammonium chloride, distillation of the ammonia and aqueous working-up, an oily product is obtained. After purification by chromatography on a 20-fold amount of silica gel using methylene chloride/methanol (10:1) for the elution, the resulting N,N-dimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine is converted into the (1:1)-maleate as described in Example 1.

Workup

  1. temperatureThe mixture is again warmed
  2. waitheld at this temperature for 0.5 hour
  3. customan oily product is obtained
  4. customAfter purification by chromatography on a 20-fold amount of silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-f23f15f27bc14039bb7dd9dfd68febd4
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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