Sodium Hydroxide → Hydrochloric Acid

HRID 354110Notes

Reaction equation

HRID 354110 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41]([Cl:43])=[O:42])=[CH:36][CH:35]=1.[OH-].[Na+]>ClCCl>[ClH:43].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][CH2:15]2)[C:41](=[O:42])[CH2:40][C:37]2[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)=[CH:6][CH:7]=1.[ClH:43]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 12146686N-[(4-Methylphenyl)methyl]-1-(phenylmethyl)-4-piperidinamine

Product 2

HCID 313Hydrochloric AcidHCID 22643491HCID 22643491, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((4-Methylphenyl)methyl)amino-1-phenylmethylpiperidine (800 mg, 2.7 mmol) in dry dichloromethane (30 ml) was added diisopropylethylamine (1.5 ml)followed by 4-methoxyphenylacetyl chloride (997 mg, 5.4 mmol). The reaction mixture was stirred at room temperature. After 16 h, the reaction mixture was concentrated, redissolved in diethyl ether, and extracted with HCl (0.6 N). The aqueous layer was isolated, treated with NaOH (1 N)until basic, and extracted with dichloromethane (20 ml). The organic layer was isolated and dried (Na2SO4), filtered, and concentrated, and redissolved in diethyl ether. The hydrochloride was formed by addition of HCl (4 M in dioxane), and recrystallized from diethyl ether to give the title compound. Yield: 600 mg, 50%; 1H-NMR (CDCl3): δ 1.75 (d, 2 H), 2.32 (s, 3 H), 2.50 (q, 2 H), 2.70 (q, 2 H), 3.38 (d, 2 H), 3.54 (s, 2 H), 3.78 (s, 3 H), 4.06 (d, 2 H), 4.54 (s, 2 H), 4.82 (m, 1 H), 6.78-7.60 (aromatic protons, 13 H); 13C-NMR (CDCl3): δ 21.0, 26.0, 40.3, 46.3, 49.0, 51.8, 55.3, 60.8, 114.2, 125.6, 126.6, 127.9, 129.4, 129.60, 129.62, 130.3, 131.4, 134.8, 137.1, 158.7, 172.9; Mp. 197-200° C.; Elemental analysis: Found C, 71.29; H, 7.25; N, 5.73; calcd for hydrate: C, 71.37; H, 7.43; N, 5.74.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionredissolved in diethyl ether
  3. extractionextracted with HCl (0.6 N)
  4. customThe aqueous layer was isolated
  5. extractionextracted with dichloromethane (20 ml)
  6. customThe organic layer was isolated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. dissolutionredissolved in diethyl ether

Sources & evidence

ORD record
ord-ecf2fa980f0249d7b9ccf983757c18de
Source dataset
uspto-grants-2004_06
Patent number
US06756393B2

Reaction notes

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