Hydrochloric Acid → N-(4-carboxybenzyl)-4-phenylbutyramide

HRID 359659Notes

Reaction equation

HRID 359659 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.Cl[Si](C)(C)C.[C:17]1([CH2:23][CH2:24][CH2:25][C:26](Cl)=[O:27])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>C(Cl)Cl.C(N(CC)CC)C>[C:7]([C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH:1][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)([OH:9])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 655264-(Aminomethyl)Benzoic AcidHCID 117898654-Phenylbutanoyl Chloride

Product 1

HCID 13922244N-(4-carboxybenzyl)-4-phenylbutyramide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-(Aminomethyl)benzoic acid (3.6 g) is suspended in methylene chloride (100 mL), to which 15 mL triethylamine is added. Chlorotrimethylsilane (10 mL) is then added and the mixture allowed to stir at room temperature for 1 hr. The mixture is then cooled in an ice bath and 4-phenylbutyryl chloride (5.3 g) in methylene chloride (10 mL) is added dropwise and the resulting mixture stirred for 30 min at 0° C., followed by an additional 3 hrs at ambient temperature. The mixture is treated with 75 mL 1 N HCl, after which the organic layer is separated and extracted with 1 N HCl. The precipitate which had formed is recovered by filtration and recrystallized two times from methanol/1 N HCl to give pure N-(4-carboxybenzyl)-4-phenylbutyramide M.p. 178°-179° C.

Workup

  1. additionis added
  2. temperatureThe mixture is then cooled in an ice bath
  3. stirringthe resulting mixture stirred for 30 min at 0° C.
  4. waitfollowed by an additional 3 hrs at ambient temperature
  5. customafter which the organic layer is separated
  6. extractionextracted with 1 N HCl
  7. customThe precipitate which had formed
  8. filtrationis recovered by filtration
  9. customrecrystallized two times from methanol/1 N HCl

Sources & evidence

ORD record
ord-cdb92cd0cf064c02be22ae436a26b2ca
Source dataset
uspto-grants-1991_03
Patent number
US05002703

Reaction notes

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