Hydrochloric Acid → 2-[4-(4-Propoxy-phenylethynyl)-phenyl]-propylamine

HRID 76173Notes

Reaction equation

HRID 76173 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:29])[CH2:20][NH:21]C(=O)OC(C)(C)C)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].Cl>CO>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[CH:15][C:16]([CH:19]([CH3:29])[CH2:20][NH2:21])=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66612060Tert-butyl 2-(4-((4-propoxyphenyl)ethynyl)phenyl)propyl-carbamate

Product 1

HCID 666107682-[4-(4-Propoxy-phenylethynyl)-phenyl]-propylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 0.70 g (1.78 mmol) tert-butyl 2-(4-((4-propoxyphenyl)ethynyl)phenyl)propyl-carbamate (I61.1) in 5 mL MeOH are added 4.27 mL (5.34 mmol) HCl (1.25M in MeOH). The mixture is stirred at r.t. over night. The solvent is removed in vacuo and the crude product is treated with aq. NaHCO3 solution. The precipitate is filtered, washed with water and dried at 50° C. in vacuo.

Workup

  1. customThe solvent is removed in vacuo
  2. additionthe crude product is treated with aq. NaHCO3 solution
  3. filtrationThe precipitate is filtered
  4. washwashed with water
  5. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-16c10aa0b2854194a16d686413dfcc83
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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