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

HRID 2287130Notes

Reaction equation

HRID 2287130 reaction equation
[CH2:1]([NH2:3])[CH3:2].Cl.[C:5]1([C:11]2([CH2:17][C:18](=O)[CH3:19])[CH:16]=[CH:15][CH2:14][CH:13]=[CH:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([BH3-])#N.[Na+]>CO>[CH3:19][CH:18]([NH:3][CH2:1][CH3:2])[CH2:17][C:11]1([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:16]=[CH:15][CH2:14][CH:13]=[CH:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 23459472(1-Phenyl-2,5-cyclohexadien-1-yl)-2-propanone

Product 1

HCID 23459459alpha-methyl-N-ethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 5.3 g. (about 8 equivalents) of ethylamine and 10 g. of molecular sieve 3A in 100 ml. absolute methanol are added at 0° C. 5.6 ml. of 5 N methanolic hydrochloric acid (2 equivalents) and then 3 g. of (1-phenyl-2,5-cyclohexadien-1-yl)-2-propanone in a small amount of absolute methanol. 0.63 g. (0.7 equivalent) of sodium cyanoborohydride is then added and the mixture is stirred at room temperature for 5 days. The mixture is worked-up in exactly the same manner as described in Example 16. The crude product is chromatographed on silica gel with methylene chloride/methanol (10:1). There is obtained α-methyl-N-ethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine as an oily product. This product is converted as usual into the hydrochloride which, after crystallization from methylene chloride/ether, has a melting point of 151°-153° C.

Workup

  1. customThe crude product is chromatographed on silica gel with methylene chloride/methanol (10:1)

Sources & evidence

ORD record
ord-558ecaeedbd6408ebe74c625e1520f7c
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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