Hydrochloric Acid → alpha,N-dimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

HRID 2287129Notes

Reaction equation

HRID 2287129 reaction equation
CN.Cl.[C:4]1([C:10]2([CH2:16][C:17](=O)[CH3:18])[CH:15]=[CH:14][CH2:13][CH:12]=[CH:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:20]([BH3-])#[N:21].[Na+]>CCOCC.CO>[CH3:18][CH:17]([NH:21][CH3:20])[CH2:16][C:10]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:15]=[CH:14][CH2:13][CH:12]=[CH:11]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 23459472(1-Phenyl-2,5-cyclohexadien-1-yl)-2-propanone

Product 1

HCID 23459460alpha,N-dimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To 11.5 ml. (about 6 equivalents) of methylamine and 10 g. of molecular sieve 3A in 200 ml. of absolute methanol are added dropwise at 0° C. 17.8 ml. of 5 N methanolic hydrochloric acid (2 equivalents) and subsequently 9.4 g. of (1-phenyl-2,5-cyclohexadien-1-yl)-2-propanone in a small amount of methanol. After the addition of 1.95 g. (0.75 equivalent) of sodium cyanoborohydride, the mixture is stirred at room temperature for 5 days. The mixture is worked-up as follows: The mixture is treated with ice-water and ether and extracted with 3 N aqueous hydrochloric acid. The hydrochloric acid extracts are made basic with concentrated aqueous ammonia and extracted with ether. The ether phase is dried with sodium sulfate, filtered and evaporated. The crude product obtained is chromatographed on silica gel with methylene chloride/methanol (10:1). There is obtained α,N-dimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine in the form of an oily product. This is converted as usual into the hydrochloride which, after crystallization from methylene chloride/ether, has a melting point of 155°-158° C.

Workup

  1. additionAfter the addition of 1.95 g
  2. extractionextracted with 3 N aqueous hydrochloric acid
  3. extractionextracted with ether
  4. dry with materialThe ether phase is dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product obtained
  8. customis chromatographed on silica gel with methylene chloride/methanol (10:1)

Sources & evidence

ORD record
ord-0d3d3d63863048dd8ea2246cf59c45ab
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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