4-Nitrophenyl chloroformate → HCID 58826198, compound

HRID 2262718Notes

Reaction equation

HRID 2262718 reaction equation
[C:1](=[O:4])(O)[O-].[Na+].[NH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.[CH:35]1([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH2:39][CH2:38][CH2:37][CH2:36]1.C(=O)(OOC1C=CC([N+]([O-])=O)=CC=1)N>C(#N)C>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([N:10]2[CH2:9][CH2:8][CH:7]([NH:6][C:1]([N:43]3[CH2:44][CH2:45][N:40]([CH:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[CH2:41][CH2:42]3)=[O:4])[CH2:12][CH2:11]2)=[CH:14][CH:15]=1)(=[O:21])[CH3:20]

Participants

7

Reactant 5

HCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 8064211-CyclopentylpiperazineHCID 574423401-[4-(4-Amino-piperidin-1-yl)-phenyl]-ethanoneHCID 86611020p-Nitrophenoxyl carbamate

Product 1

HCID 58826198HCID 58826198, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a suspension of sodium bicarbonate (40 mmol) in acetonitrile (50 mL) is added hydrochloride salt of 1-[4-(4-amino-piperidin-1-yl)-phenyl]-ethanone (10 mmol) and p-nitrophenyl chloroformate (10 mmol) at 0° C. The mixture is stirred at rt for 1 hour. A solution of 1-cyclopentylpiperazine (10.5 mmol) and TEA (25 mmol) in acetonitrile (15 mL) is added to the mixture at rt. The resulting mixture is stirred until no p-nitrophenoxyl carbamate remained by TLC. The mixture is then concentrated, diluted with EtOAc (100 mL) and washed with aqueous potassium carbonate (2×80 mL), and dried over MgSO4. Removal of the solvent, followed by PTLC purification gives the title compound. 1H NMR (300 MHz, CDCl3) δ 7.85 (d, 2H), 6.84 (d, 2H), 4.41 (d, 1H), 3.81-3.98 (m, 3H), 3.52-3.40 (m, 4H), 3.02 (t, 2H), 2.2.66-2.43 (m, 8H), 2.15-2.01 (m, 2H), 1.97-1.82 (m, 2H), 1.78-1.64 (m, 2H), 1.60-1.41 (m, 6H); LC-MS (M+1) 399.5.

Workup

  1. concentrationThe mixture is then concentrated
  2. additiondiluted with EtOAc (100 mL)
  3. washwashed with aqueous potassium carbonate (2×80 mL)
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent
  6. customfollowed by PTLC purification

Sources & evidence

ORD record
ord-696a7c09302743329f72be3cfc565780
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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