HCID 12362579, compound → 3-Phenyl-3H-spiro[2-benzofuran-1,4'-piperidin]-1'-amine

HRID 2398281Notes

Reaction equation

HRID 2398281 reaction equation
[N:1]([N:3]1[CH2:8][CH2:7][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:9]2)[CH2:5][CH2:4]1)=O>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(O)(=O)C.O.[Zn]>[NH2:1][N:3]1[CH2:4][CH2:5][C:6]2([C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:9]2)[CH2:7][CH2:8]1

Participants

6

Reactant 1

HCID 12362579HCID 12362579, compound

Product 1

HCID 30461803-Phenyl-3H-spiro[2-benzofuran-1,4'-piperidin]-1'-amine

Reagents, catalysts & solvents 4

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

A solution of 7.1 g of 1'-nitroso-1,3-dihydro-3-phenylspiro[isobenzofuran-1,4'-piperidine], Example 1, in 75 ml of glacial acetic is added to a stirring suspension pf 7.1 g of zinc dust in 50 ml of glacial acetic acid and 50 ml of water while maintaining the reaction temperature between 10° and 20° C. The reaction mixture is stirred for 15 minutes at ambient temperature and then at 80° C. for 5 minutes; an additional 4.7 g of zinc dust are introduced and stirring is continued for an additional 10 minutes. The heated mixture is filtered, the precipitate is washed with hot 1N hydrochloric acid and the combined filtrate and washings are basified and extracted with chloroform. The organic solution is dried and the solvent is removed, leaving a white crystalline solid, 1'-amino-1,3-dihydro-3-phenylspiro[isobenzofuran-1,4'-piperidine], which is recrystallized from ethanolto to give the pure product, mp 143°-145° C.

Workup

  1. temperaturewhile maintaining the reaction temperature between 10° and 20° C
  2. waitat 80° C. for 5 minutes
  3. stirringstirring
  4. waitis continued for an additional 10 minutes
  5. filtrationThe heated mixture is filtered
  6. washthe precipitate is washed with hot 1N hydrochloric acid
  7. extractionextracted with chloroform
  8. customThe organic solution is dried
  9. customthe solvent is removed

Sources & evidence

ORD record
ord-577311e04b2b42a5951f92337cdfa47b
Source dataset
uspto-grants-1977_05
Patent number
US04024263

Reaction notes

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