Ammonia → HCID 21764421, compound

HRID 2287128Notes

Reaction equation

HRID 2287128 reaction equation
Cl.[C:2]1([C:8]2([CH2:14][CH2:15]N)[CH:13]=[CH:12][CH2:11][CH:10]=[CH:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([BH3-])#[N:18].[Na+].Cl.N.[CH3:23]O>>[CH3:23][N:18]([CH3:17])[CH2:15][CH2:14][C:8]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][CH2:11][CH:10]=[CH:9]1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 23459461HCID 23459461, compound

Product 1

HCID 21764421HCID 21764421, compound

Procedure

4 g. of 1-phenyl-2,5-cyclohexadien-1-ethylamine hydrochloride are placed in 100 ml. of absolute methanol. After the addition of 3.3 g. (6.5 equivalents) of p-formaldehyde, 1 g. (about 1 equivalent) of sodium cyanoborohydride and 5 g. of molecular sieve 3A, the mixture is stirred at room temperature overnight and subsequently worked-up as follows: The mixture is poured into aqueous 3 N hydrochloric acid, stirred for 10 minutes, made basic with concentrated aqueous ammonia, extracted with ethyl acetate, washed with water, dried with sodium sulfate and filtered. There is obtained an oily product which is chromatographed on 80 g. of silica gel with methylene chloride/methanol (10:1). The yellow oil obtained (N,N-dimethyl-1-phenyl-2,5-cyclohexadien-1-ethylamine) is converted in the customary manner into the (1:1)-maleate which has a melting point of 129°-131° C.

Workup

  1. additionAfter the addition of 3.3 g
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customThere is obtained an oily product which
  7. customis chromatographed on 80 g

Sources & evidence

ORD record
ord-55bdcb3909ad486a8cc09e476e46aa33
Source dataset
uspto-grants-1981_05
Patent number
US04269788

Reaction notes

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