Triethylamine → HCID 5459455, compound

HRID 2108330Notes

Reaction equation

HRID 2108330 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C(N(CC)CC)C.[N:21]1([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C1COCC1>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([N:30]2[CH2:31][CH2:32][CH:27]([N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:28][CH2:29]2)=[O:3])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 786071,4'-BipiperidineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 5459455HCID 5459455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-nitrophenyl chloroformate (31) (5.15 g, 25.6 mmol) in 150 mL of dry THF at −78° C. was added triethylamine (10.7 mL, 76.2 mmol), followed by a solution of 4-piperidinopiperidine (30) (4.51 g, 25.6 mmol) in 40 mL of THF. This solution was stirred for two hours, after which the solvent was removed, and the residue was taken up in AcOEt, filtered and evaporated. The crude yellow solid was passed through a pad of neutral alumina using AcOEt as an eluent to yield, after evaporation, 6.73 g (79%) of a white solid: IR (CHCl3, cm−1) 3046, 2937, 2859, 1704, 1620, 1513, 1466, 1242, 1197; 1H NMR (300 MHz, CDCl3) δ 1.20-1.80 (m, 8 H), 1.90 (d, J=12.7 Hz, 2 H), 2.20-2.70 (m, 5 H), 2.87 (t, J=12 Hz, 1 H), 3.01 (t, J=12 Hz, 1 H), 4.30 (br s, 2 H), 7.29 (d, J=9 Hz, 2 H), 8.26 (d, J=9 Hz, 2 H); 13C NMR (75 MHz, CDCl3) δ 24.6, 26.3, 27.5, 28.2, 40.1, 44.4, 50.1, 62.0, 122.2, 124.9, 144.8, 151.9, 156.3; HRMS (EI) m/z calcd for C17H23N3O4 (M+) 333.1676, found 333.1688; LRMS (EI) m/z 333 (M+), 195, 167, 124, 110, 96, 55.

Workup

  1. customafter which the solvent was removed
  2. filtrationfiltered
  3. customevaporated
  4. customto yield
  5. customafter evaporation, 6.73 g (79%) of a white solid

Sources & evidence

ORD record
ord-de2e6c419f5b4b82bb50fbf0d6da7a51
Source dataset
uspto-grants-2009_04
Patent number
US07514418B2

Reaction notes

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