Hydrochloric Acid → HCID 10803968, compound

HRID 1004660Notes

Reaction equation

HRID 1004660 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[O:28]([CH2:35][CH2:36][CH2:37][NH2:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>O1CCCC1.[Cl-].[Na+].O>[O:28]([CH2:35][CH2:36][CH2:37][NH:38][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 739273-(p-Tolyl)propionic acidHCID 418237(3-Phenoxypropyl)amine

Product 1

HCID 10803968HCID 10803968, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-methylbenzenepropanoic acid (2.0 g, 12.2 mmol) and triethylamine (4.3 mL, 3.1 g, 30.9 mmol) in 80 mL of tetrahydrofuran is cooled in ice and treated dropwise with isobutyl chloroformate (1.7 mL, 1.8 g, 13.1 mmol). The mixture is stirred for 1 hour, and a solution of 3-phenoxy-1-propanamine (1.9 g, 12.6 mmol) in 10 mL of tetrahydrofuran is added slowly. The mixture is stirred at room temperature for 18 hours, then added to 400 mL of brine. The mixture is acidified with 4.0 N hydrochloric acid and extracted with ethyl acetate. The combined organic layers are washed with brine, dried (anhydrous sodium sulfate), and evaporated. Recrystallization of the residue gives 2.2 g (61%) of the amide intermediate product, mp 101-102° C.

Workup

  1. stirringThe mixture is stirred at room temperature for 18 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried (anhydrous sodium sulfate)
  5. customevaporated
  6. customRecrystallization of the residue

Sources & evidence

ORD record
ord-79cf617ba86e4854be7b9e82ccf85aa8
Source dataset
uspto-grants-2000_04
Patent number
US06051605

Reaction notes

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