Triethylamine → HCID 3913788, compound

HRID 243561Notes

Reaction equation

HRID 243561 reaction equation
CCN(CC)CC.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=O)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[O:46]1[CH2:51][CH2:50][N:49]([CH2:52][CH2:53][CH2:54][NH2:55])[CH2:48][CH2:47]1>CN(C=O)C>[O:46]1[CH2:51][CH2:50][N:49]([CH2:52][CH2:53][CH2:54][NH:55][C:21]([CH:18]2[CH2:17][CH2:16][N:15]([C:13]([O:12][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:14])[CH2:20][CH2:19]2)=[O:23])[CH2:48][CH2:47]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 61055N-(3-Aminopropyl)morpholineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 3913788HCID 3913788, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NEt3 (1.8 ml) is added to a solution of 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1.5 g) in DMF (40 ml) and the mixture is stirred for 10 min. TBTU (3.15 g) is added, and after additional 10 min the 3-morpholinopropan-1-amine (0.98 ml) is added. The reaction mixture is stirred over night and the solvent is removed under reduced pressure. The residue is dissolved in EtOAc and washed with satd. aqueous NaHCO3, aqueous citric acid (10%) and brine, dried (MgSO4) and filtered, and the solvent is removed under reduced pressure to give crude tert-butyl 4-(3-morpholinopropylcarbamoyl)piperidine-1-carboxylate (2.3 g). The crude product is used without purification in the next step.

Workup

  1. stirringThe reaction mixture is stirred over night
  2. customthe solvent is removed under reduced pressure
  3. dissolutionThe residue is dissolved in EtOAc
  4. washwashed with satd
  5. dry with materialaqueous NaHCO3, aqueous citric acid (10%) and brine, dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-505f1106e5ea48fab38a439c718dbec0
Source dataset
uspto-grants-2014_02
Patent number
US08653262B2

Reaction notes

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