Formaldehyde → HCID 13755881, compound

HRID 2231627Notes

Reaction equation

HRID 2231627 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:8]([C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH2:18][C:19]2=[O:22])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].[CH2:23]=O>C(O)C.Cl>[C:8]([C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([CH2:23][N:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)[C:19]2=[O:22])=[CH:14][CH:13]=1)([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 6045627-tert-Butyl-1-tetraloneHCID 2723721Piperidine, hydrochloride (1:1)

Product 1

HCID 13755881HCID 13755881, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

Piperidine hydrochloride (8.9 g, 0.073 mol), 7-tert-butyl-1,2,3,4-tetrahydronaphthalene-1-one (7.0 g, 0.035 mol) and paraformaldehyde (2.2 g, 0.073 mol) were refluxed together in ethanol (150 ml) along with concentrated hydrochloric acid (1 ml) as a catalyst for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water then extracted with diethyl ether. The resulting aqueous solution was neutralized with sodium bicarbonate and extracted with diethyl ether (2×200 ml), dried over magnesium sulphate and concentrated under reduced pressure to give 7-tert-butyl-2-piperidinomethyl-1,2,3,4-tetrahydronaphthalen-1-one (4.5 g, 43% yield) as a buff coloured solid melting at 62°-3°. Compound number 4 in Table I.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue dissolved in water
  3. extractionthen extracted with diethyl ether
  4. extractionextracted with diethyl ether (2×200 ml)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f52ca6a850449a7ba4ebd1b1a9e3fc2
Source dataset
uspto-grants-1988_11
Patent number
US04783458

Reaction notes

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