3,4-Dihydro-1'-(phenylmethyl)spiro[naphthalene-1(2H),4'-piperidine] → HCID 15637617, compound

HRID 507285Notes

Reaction equation

HRID 507285 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[NH:8]1[CH2:13][CH2:12][C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 1253283,4-Dihydro-1'-(phenylmethyl)spiro[naphthalene-1(2H),4'-piperidine]HCID 2723923Ammonium formate

Product 1

HCID 15637617HCID 15637617, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1′-benzyl-3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine] 17a (1.7 g, 5.8 mmol), 10% Pd/C (1 g), and ammonium formate (4.8 g, 76 mmol) in MeOH (50 ml) was stirred under N2 for 24 hours. The mixture was filtered through Celite, and the filtrate was concentrated. The filtrate was dissolved in CH2Cl2, washed with diluted NaOH, and the aqueous phase was re-extracted with CH2Cl2. The combined organic phase was dried (Na2SO4) and concentrated to give 3,4-dihydro-2H-spiro[naphthalene-1,4′-piperidine] 17b. LC-MS: m/e=202.1 (M+H). Rt=1.61 min. 1H-NMR (500 MHz, CDCl3): 9.74 (s, 2H), 7.58 (d, J=7.9, 1H), 7.22 (t, J=7.8, 1H), 7.14 (t, J=7.9, 1H), 7.08 (d, J=8.0, 1H), 3.47 (d, J=12.4, 2H), 3.22-3.18 (m, 2H), 2.88 (t, J=4.9, 2H), 2.81 (t, J=6.2, H), 2.60 (td, 2H), 1.93-1.89 (m, 2H), 1.83-1.77 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe filtrate was dissolved in CH2Cl2
  4. washwashed with diluted NaOH
  5. extractionthe aqueous phase was re-extracted with CH2Cl2
  6. dry with materialThe combined organic phase was dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ad2a7762c99f4bd6aa3b5df3f33c15ac
Source dataset
uspto-grants-2010_08
Patent number
US07786141B2

Reaction notes

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