Formaldehyde → HCID 13755882, compound

HRID 867872Notes

Reaction equation

HRID 867872 reaction equation
[C:1]([C:5]1[CH:14]=[C:13]2[C:8]([C:9](C)=[C:10]([CH2:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:11][CH2:12]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.N1CCCCC1.C(C1C=C2C(=CC=1)C(=[O:44])CCC2)(C)(C)C.C=O>C(O)C.Cl>[C:1]([C:5]1[CH:14]=[C:13]2[C:8](=[CH:7][CH:6]=1)[C:9](=[O:44])[CH:10]([CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:11][CH2:12]2)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 6045571(2H)-Naphthalenone, 6-(1,1-dimethylethyl)-3,4-dihydro-HCID 2723721Piperidine, hydrochloride (1:1)HCID 21289050HCID 21289050, compound

Product 1

HCID 13755882HCID 13755882, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

This Example illustrates the preparation of 7-tert-butyl-4-methyl-3-piperidinomethyl,1,2-dihydronaphthalene (Compound number 3 of Table I). Piperidine hydrochloride (12.6 g 0.103 mol), 6-tert-butyl-1,2,3,4-tetrahydronaphthalen-1-one (80.0 g, 0.04 mol) and paraformaldehyde (2.64 g, 0.088 mol) were refluxed in ethanol (200 ml) with concentrated hydrochloric acid (1 ml) as a catalyst for 48 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); the ethereal extracts were dried over magnesium sulphate and concentrated under reduced pressure to give 6-tert-butyl-2-piperidinomethyl-1,2,3,4-tetrahydronaphthalen-1-one (10.0 g 83% yield) melting at 47°-9°.

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 materialthe ethereal extracts were dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b54720178804ca0a63c104680d99687
Source dataset
uspto-grants-1988_10
Patent number
US04777176

Reaction notes

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