Benzylamine → HCID 16794071, compound

HRID 1609825Notes

Reaction equation

HRID 1609825 reaction equation
[C:1]([C:3]1([NH:12]C(=O)C(O)CC(C)C)[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH3:11])[CH2:5][CH2:4]1)#[N:2].ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.CN1CCOCC1.C(N)C1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH2:12][C:3]1([C:1]#[N:2])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH3:11])[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 23589512HCID 23589512, compound

Product 1

HCID 16794071HCID 16794071, compoundYield 108.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-hydroxy-4-methyl-pentanoic acid (4-cyano-1-propyl-piperidin-4-yl)-amide (0.316 g, 1.1 mmol) in CH2Cl2 (30 mL) was added DMAP (0.192 g, 1.6 mmol), p-nitrophenyl chloroformate (0.249 g, 1.2 mmol), and N-methylmorpholine (0.136 mL, 1.2 mmol). The resulting mixture was allowed to stir overnight (20 h) under argon at room temperature, then treated with benzylamine (1.68 g, 16 mmol) and allowed to stir overnight (20 h). When the reaction was complete the mixture was diluted with CH2Cl2 (50 mL), then washed with saturated aq. NaHCO3 (50 mL), water and brine, dried over Na2SO4, filtered and evaporated in vacuo to give 0.200 g (50% yield) of the desired product after purification by prep-HPLC;

Workup

  1. stirringto stir overnight (20 h)
  2. washwashed with saturated aq. NaHCO3 (50 mL), water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0e398cdc98c74411b582e609edc53b5f
Source dataset
uspto-grants-2006_01
Patent number
US06982263B2

Reaction notes

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