Diisopropylethylamine → HCID 66593418, compound

HRID 1091655Notes

Reaction equation

HRID 1091655 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[C:25]([N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C@@H:33]1[C:38]([OH:40])=O)([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].CCN(C(C)C)C(C)C.[N+:50]([C:53]1[CH:58]=[C:57]([NH2:59])[CH:56]=[CH:55][C:54]=1[NH2:60])([O-:52])=[O:51]>CN(C=O)C>[NH2:60][C:54]1[CH:55]=[CH:56][C:57]([NH:59][C:38]([C@H:33]2[CH2:34][CH2:35][CH2:36][CH2:37][N:32]2[C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])=[O:40])=[CH:58][C:53]=1[N+:50]([O-:52])=[O:51]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 688618(2R)-1-[(tert-butoxy)carbonyl]piperidine-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 43383702-Nitro-4-phenylenediamine

Product 1

HCID 66593418HCID 66593418, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU, 4.96 g, 13.1 mmol) was added to a stirred solution of (R)—N-Boc-2-piperidinecarboxylic acid (3.00 g, 13.1 mmol) and DIPEA (9.0 mL, 51.2 mmol) in anhydrous DMF (50 mL). The mixture was stirred at room temperature for 5 min and then 2-nitro-1,4-phenylenediamine (3.00 g, 13.1 mmol) was added. The mixture was stirred for a further 18 hr, then the DMF was removed by evaporation. The residue was partitioned between water (200 mL) and EA (100 mL) and the phases separated. The aqueous phase was extracted with two further portions of EA (100 mL each) and the combined organic extracts washed with water, 1M sodium carbonate solution, water, and brine (100 mL each). The solution was dried over magnesium sulfate and concentrated to give (R)-tert-butyl 2-[(4-amino-3-nitrophenyl)aminocarbonyl]-piperidine-1-carboxylate as a brown solid (4.80 g).

Workup

  1. stirringThe mixture was stirred for a further 18 hr
  2. customthe DMF was removed by evaporation
  3. customThe residue was partitioned between water (200 mL) and EA (100 mL)
  4. customthe phases separated
  5. extractionThe aqueous phase was extracted with two further portions of EA (100 mL each)
  6. washthe combined organic extracts washed with water, 1M sodium carbonate solution, water, and brine (100 mL each)
  7. dry with materialThe solution was dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-19aae0e8f7494e3eb79d730467e25a0b
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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