Hydrochloric Acid → HCID 18975689, compound

HRID 2393463Notes

Reaction equation

HRID 2393463 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 product 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 light petroleum and dried in vacuo to give N-[2-(4-methoxyphenyl)ethyl]cyclobutanecarboxamide (9.54 g), mp 118°-120° C.

Workup

  1. additionpoured onto water
  2. extractionthe product 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 light petroleum
  8. customdried in vacuo

Sources & evidence

ORD record
ord-fd728829627c485180454d2a3f3c3f78
Source dataset
uspto-grants-1998_09
Patent number
US05807868

Reaction notes

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