Hydrochloric Acid → 1-(4-Iodobenzoyl)piperidine

HRID 568884Notes

Reaction equation

HRID 568884 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.Cl>C(N(CC)CC)C>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 743734-Iodobenzoyl chloride

Product 1

HCID 51492041-(4-Iodobenzoyl)piperidineYield 78.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Iodobenzoyl chloride (10.0 g) was added portionwise to piperidine (3.53 g) in triethylamine (40 ml) at 0° and the suspension was stirred at room temperature under nitrogen for 1 h. The reaction mixture was poured into 2N aqueous hydrochloric acid (200 ml) and extracted with EA (3×100 ml). The combined extracts were washed with water (100 ml), 8% aqueous sodium bicarbonate (100 ml) and water (10 ml), dried and concentrated. The resultant solid (10.25 g) was purified by FCC eluting with ER-H (1:2→1:1) to give the title compound as a white solid (9.33 g) m.p. 126°-127°.

Workup

  1. extractionextracted with EA (3×100 ml)
  2. washThe combined extracts were washed with water (100 ml), 8% aqueous sodium bicarbonate (100 ml) and water (10 ml)
  3. customdried
  4. concentrationconcentrated
  5. customThe resultant solid (10.25 g) was purified by FCC
  6. washeluting with ER-H (1:2→1:1)

Sources & evidence

ORD record
ord-9ebe51f768d941d0af16404fb703d030
Source dataset
uspto-grants-1988_03
Patent number
US04730008

Reaction notes

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