Water → HCID 54431841, compound

HRID 846248Notes

Reaction equation

HRID 846248 reaction equation
[CH2:1]([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:18]1([CH2:24][C:25]#[N:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+].O>CO>[CH2:1]([O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[C:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:25]#[N:26])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8794PhenylacetonitrileHCID 14798Sodium HydroxideHCID 90358p-(Octyloxy)benzaldehyde

Product 1

HCID 54431841HCID 54431841, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 117 g of 4-octyloxybenzaldehyde and 58.5 g of phenylacetonitrile in methanol was stirred at room temperature and aqueous (50 percent) sodium hydroxide was added dropwise. The addition of base was stopped upon formation of a precipitate and the resultant mixture was stirred overnight at room temperature. The mixture was then poured into a large volume of water and fitered to collect the solids which were washed with water to yield the intermediate, α-[[4-(octyloxy)phenyl]methylene]benzeneacetonitrile. 101.5 Grams of this intermediate nitrile, 25 g of Raney nickel, 150 ml of anhydrous ammonia and 200 ml of tetrahydrofuran were stirred at 140° C. for 10 hours at a pressure of 2,000 psi. The catalyst and solvent were then removed and the residue was taken up in diethyl ether and then filtered through magnesia-silica gel. The hydrochloride salt of the title compound was made in the filtrate by the addition of anhydrous hydrochloric acid. The hydrochloride salt was recovered by recrystallization from ethanol to yield 4-(octyloxy)-β-phenylbenzenepropanamine hydrochloride (18 percent yield), m.p. 127°, decomposition (dec.).

Workup

  1. additionThe addition of base
  2. customto collect the solids which
  3. washwere washed with water

Sources & evidence

ORD record
ord-c1339ff9c20b4a02b99982924c14d33c
Source dataset
uspto-grants-1992_08
Patent number
US05135955

Reaction notes

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