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4-(4-Piperidyl)pyridine → 1-Tert-butoxycarbonyl-4-[4-(4-pyridyl)-1-piperidylmethyl]piperidine

HRID 1936570
Notes
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Reaction equation

HRID 1936570 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:25]2[CH2:26][CH2:27][CH:22]([C:19]3[CH:18]=[CH:17][N:16]=[CH:21][CH:20]=3)[CH2:23][CH2:24]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11395974-(4-Piperidyl)pyridineHCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 183289141-Tert-butoxycarbonyl-4-[4-(4-pyridyl)-1-piperidylmethyl]piperidineYield 37.8%

Reagents, catalysts & solvents 1

HCID 10129899Acetic acid methanol
Solvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(formyl)piperidine (2.59 g) and 4-(4-pyridyl)piperidine (1.97 g) in methanol/acetic acid (99:1) (50 ml) was added sodium cyanoborohydride (2.29 g) portionwise over 30 minutes and the resultant suspension stirred at ambient temperature for 3 hours. The suspension was quenched by addition of saturated aqueous sodium bicarbonate and the resulting mixture extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated, The residue was purified by chromatography eluting with 5% methanol in dichloromethane to give 1-[1-tert-butoxycarbonyl(4-piperidinylmethyl)]-4-(4-pyridyl)piperidine (1.65 g) as a solid: NMR (CDCl3): 1.10 (m, 2H), 1.40 (s, 9H), 1.75 (m, 7H), 2.00 (dt, 2H), 2.20 (d, 2H), 2.45 (m, 1H), 2.70 (m, 2H), 3.00 (d, 2H), 4.10 (m, 2H), 7.20 (d, 2H), 8.50 (d, 2H); m/z 360 (M+1).

Workup

  1. customThe suspension was quenched by addition of saturated aqueous sodium bicarbonate
  2. extractionthe resulting mixture extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by chromatography
  6. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-72443b31294c4750a407dac815a56fe8
Source dataset
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06391880B1

Reaction notes

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