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

HRID 383870Notes

Reaction equation

HRID 383870 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-1774b5bf2c854b58b5a8075686134199
Source dataset
uspto-grants-2013_02
Patent number
US08367691B2

Reaction notes

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