Hydrochloric Acid → HCID 18975689, compound

HRID 2393111Notes

Reaction equation

HRID 2393111 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][CH:11]=1.C(N(CC)CC)C.Cl>CCOCC>[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][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4657O-MethyltyramineHCID 8471TriethylamineHCID 78705Cyclobutanecarbonyl chloride

Product 1

HCID 18975689HCID 18975689, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Cyclobutanecarbonyl chloride (5.5 g) was added to a solution of 2-(4-methoxyphenyl)ethylamine (7 g) and triethylamine (6.5 ml) in ether (300 ml) at ambient temperature. The mixture was stirred overnight, poured onto water and acidified with 2M hydrochloric acid, then the mixture was extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine, dried and the solvents removed in vacuo to give a residue. This was washed with petroleum ether and dried in vacuo to give N-[2-(4-methoxyphenyl)ethyl]cyclobutanecarboxamide as a solid (9.54 g), mp 118°-120° C.

Workup

  1. additionpoured onto water
  2. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  3. washThe combined extracts were washed with brine
  4. customdried
  5. customthe solvents removed in vacuo
  6. customto give a residue
  7. washThis was washed with petroleum ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-58345fbe44554570a94066a7a1e2a2f5
Source dataset
uspto-grants-1998_09
Patent number
US05804586

Reaction notes

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