Hydrochloric Acid → [2-(4-Methoxyphenyl)-naphthalen-1-yl][4-[2-(1-pyrrolidinyl)ethoxy]phenyl]methane hydrochloride

HRID 742345Notes

Reaction equation

HRID 742345 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)O)=[CH:5][CH:4]=1.[ClH:35]>CO>[ClH:35].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH2:19][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:23][CH:22]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10182739[2-(4-Methoxyphenyl)-3,4-dihydronaphth-1-yl][4-(1-pyrrolidinyl-2-ethoxy)phenyl]carbinol

Product 1

HCID 18458660[2-(4-Methoxyphenyl)-naphthalen-1-yl][4-[2-(1-pyrrolidinyl)ethoxy]phenyl]methane hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of the product of Example 14 (2.0 g, 4.58 mmol) stirring in methanol (50 mL) at ambient temperature was added methanolic hydrochloric acid (10 mL of a saturated solution). The reaction mixture was then concentrated to 20 mL and cooled to -20° C. for several hours. Filtration gave 0.62 g of the desired product as a white powder: 1 -NMR (CDCl3, 300 MHz) consistent with structure; MS (FD) m/e 437 (M+ -hydrochloric acid); Anal. Calc'd. for: C, 76.01; H, 6.80; N, 2.96. Found: C, 75.95; H, 6.76; N, 2.98.

Workup

  1. concentrationThe reaction mixture was then concentrated to 20 mL
  2. filtrationFiltration

Sources & evidence

ORD record
ord-03d0a9d8e46e4410b0b03c15a92f92f9
Source dataset
uspto-grants-1996_09
Patent number
US05554628

Reaction notes

Loading…