Hydrochloric Acid → HCID 18975719, compound

HRID 2393456Notes

Reaction equation

HRID 2393456 reaction equation
[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH2:18])=[CH:12][C:11]=1[CH3:19].C(N(CC)CC)C.Cl>O1CCCC1.O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][NH:18][C:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[O:6])=[CH:12][C:11]=1[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chlorideHCID 64846602-(4-Methoxy-3-methylphenyl)ethan-1-amine

Product 1

HCID 18975719HCID 18975719, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclobutanecarbonyl chloride (7 g) was added dropwise to a solution of 2-(4-methoxy-3-methylphenyl)ethylamine (11.36 g) and triethylamine (13 ml) in tetrahydrofuran (150 ml) and the resulting suspension stirred for 16 hours. The mixture was poured into water (150 ml), acidified with dilute hydrochloric acid and extracted with ethyl acetate (4×50 ml). The combined organic extracts were washed with brine then dried over magnesium sulphate and the solvent removed in vacuo. The residue was washed with petroleum ether (bp 40°-60° C.) to give crude N-[2-(4-methoxy-3-methylphenyl)ethyl]cyclobutanecarboxamide (12 g). A sample recrystallised from acetonitrile had mp 103°-104° C.

Workup

  1. extractionextracted with ethyl acetate (4×50 ml)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialthen dried over magnesium sulphate
  4. customthe solvent removed in vacuo
  5. washThe residue was washed with petroleum ether (bp 40°-60° C.)

Sources & evidence

ORD record
ord-7e0fa43e788244fda70089cacf401c8b
Source dataset
uspto-grants-1998_09
Patent number
US05807868

Reaction notes

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