Hydrochloric Acid → alpha-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine hydrochloride

HRID 2287134Notes

Reaction equation

HRID 2287134 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[ClH:6].[C:7]1([C:13]2([CH2:19][C:20](=O)[CH3:21])[CH:18]=[CH:17][CH2:16][CH:15]=[CH:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([BH3-])#N.[Na+]>CO>[ClH:6].[CH3:21][CH:20]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[CH2:19][C:13]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:18]=[CH:17][CH2:16][CH:15]=[CH:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 5003444Sodium cyanoborohydrideHCID 23459472(1-Phenyl-2,5-cyclohexadien-1-yl)-2-propanone

Product 1

HCID 23459443alpha-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 27.5 ml. (about 6 equivalents) of diethylamine and 10 g. of molecular sieve 3A in 200 ml. of methanol are added at 0° C. 17.6 ml. of 5 N methanolic hydrochloric acid (2 equivalents) and then 9.4 g. of (1-phenyl-2,5-cyclohexadien-1-yl)-2-propanone in a small amount of methanol and finally 1.95 g. (0.7 equivalents) of sodium cyanoborohydride. The mixture is stirred at room temperature for 5 days and then worked-up in exactly the same manner as described in Example 16. There is obtained an oily residue which is chromatographed on a silica gel thick-layer plate with ethyl acetate/triethylamine (15:1). Two products are scratched off and eluted with methylene chloride/methanol (4:1). The product of RF 0.32 is α-methyl-N-ethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine. The other product (RF 0.54) is the desired product, namely, α-methyl-N,N-diethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine. This is converted as usual into the hydrochloride and recrystallized from methylene chloride/ether. According to melting point and mixed melting point, the product is identical with that obtained in accordance with Example 18.

Workup

  1. customThere is obtained an oily residue which
  2. customis chromatographed on a silica gel thick-layer plate with ethyl acetate/triethylamine (15:1)
  3. washeluted with methylene chloride/methanol (4:1)
  4. customrecrystallized from methylene chloride/ether
  5. additionmixed
  6. customthat obtained in accordance with Example 18

Sources & evidence

ORD record
ord-026ead067bc74d2f84a5ace4bba0b2d9
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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