Diisopropylethylamine → N-(3-tert-butoxycarbonylaminopropyl)-4-cyano-4-(o-tolyl)piperidine

HRID 650526Notes

Reaction equation

HRID 650526 reaction equation
[C:1]([C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)#[N:2].[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26]Br)=[O:22])([CH3:19])([CH3:18])[CH3:17].C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:16]([O:20][C:21]([NH:23][CH2:24][CH2:25][CH2:26][N:6]1[CH2:7][CH2:8][C:3]([C:1]#[N:2])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[CH2:4][CH2:5]1)=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 101765704-o-Tolylpiperidine-4-carbonitrile

Product 1

HCID 21712249N-(3-tert-butoxycarbonylaminopropyl)-4-cyano-4-(o-tolyl)piperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-cyano-4-(o-tolyl)piperidine (5.00 g, 24.9 mmol) and 1-(tert-butoxycarbonylamino)-3-bromopropane (16, 6.55 g, 27.5 mmol) in DMF (100 mL) was treated with diisopropylethylamine (4.50 mL, 25.8 mmol) at room temperature. The resulting mixture was stirred at room temperature (3 d). The solvent was removed in vacuo and the residue dissolved in dichloromethane and sodium bicarbonate solution. The aqueous layer was extracted with two additional portions of dichloromethane and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flash chromatography on silica gel (5% methanol/dichloromethane) afforded the title compound (25).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in dichloromethane
  3. extractionThe aqueous layer was extracted with two additional portions of dichloromethane
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-147422ddf5a84e54949323a0cc52a38b
Source dataset
uspto-grants-2001_08
Patent number
US06274583B1

Reaction notes

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