Piperidine → (1-Isopropylpiperidin-4-yl)(4-(piperidin-1-ylmethyl)phenyl)methanone

HRID 560987Notes

Reaction equation

HRID 560987 reaction equation
[Na+].O[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([CH:22]([CH3:24])[CH3:23])[CH2:18][CH2:17]2)=[O:15])=[CH:10][CH:9]=1)S([O-])(=O)=O.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[CH:22]([N:19]1[CH2:20][CH2:21][N:16]([C:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:3][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:9][CH:10]=2)=[O:15])[CH2:17][CH2:18]1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 59340029Hydroxy-[4-(4-isopropyl-piperazine-1-carbonyl)-phenyl]-methanesulfonic acid sodium salt

Product 1

HCID 10359235(1-Isopropylpiperidin-4-yl)(4-(piperidin-1-ylmethyl)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of hydroxyl-[4-(4-isopropyl-piperazine-1-carbonyl)-phenyl]-methanesulfonic acid sodium salt (54.6 g, 0.150 mol), piperidine (28.0 g, 0.330 mol), and Montmorillonite-K10 (10.9 g, 20% by wt. relative to starting material) in dichloroethane (820 mL) was stirred at room temperature for 16 h. NaBH(OAc)3 (44.5 g, 210.0 mmol) was added in portions over 1 h, and the resulting suspension was stirred at room temperature for 5 h. Diatomaceous earth (5.4 g) was added and the suspension was stirred for an additional 30 min. The reaction mixture was filtered through a pad of diatomaceous earth, rinsing with dichloroethane (2×100 mL). The filtrate was washed with 1 N NaOH (2×200 mL). The aqueous layers were combined and back-extracted with dichloroethane (2×100 mL). The organic layers were combined, dried (Na2SO4), and concentrated to yield the title compound as its corresponding free base, as a pale yellow oil.

Workup

  1. stirringthe resulting suspension was stirred at room temperature for 5 h
  2. additionDiatomaceous earth (5.4 g) was added
  3. stirringthe suspension was stirred for an additional 30 min
  4. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  5. washrinsing with dichloroethane (2×100 mL)
  6. washThe filtrate was washed with 1 N NaOH (2×200 mL)
  7. extractionback-extracted with dichloroethane (2×100 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e43d5b46d167462b89b0e809a7a31aa9
Source dataset
uspto-grants-2011_11
Patent number
US08063206B2

Reaction notes

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