1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → HCID 69016012, compound

HRID 1455050Notes

Reaction equation

HRID 1455050 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[O:15][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]3)=[N:6][CH:7]=1.[C:25]([O:29][C:30]([N:32]1[CH2:40][CH2:39][CH:35]([C:36](O)=[O:37])[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].Cl.CN(C)CCCN=C=NCC>C1COCC1>[C:25]([O:29][C:30]([N:32]1[CH2:40][CH2:39][CH:35]([C:36](=[O:37])[NH:1][C:2]2[CH:7]=[N:6][C:5]([O:8][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][CH:18]=3)[O:15][CH:14]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:13][CH2:12]4)=[CH:4][CH:3]=2)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 179784785-Amino-2-(2-phenylchroman-6-yloxy)pyridine

Product 1

HCID 69016012HCID 69016012, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-2-(2-phenylchroman-6-yloxy)-pyridine (500 mg) and N-(tert-butoxycarbonyl)isonipecotic acid (541 mg) was dissolved in 40 ml of THF. 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (451 mg) was added. The mixture was refluxed for few hours. Reaction was quenched with addition of water and extracted with ethyl acetate. Combined organic layers were washed with water, saturated sodium carbonate solution, dried with Na2SO4 and evaporated. 1H-NMR (300 MHz; d6-DMSO) δ: 10.0 (s, 1H), 8.31 (d, 1H, J 2.7 Hz), 8.03 (dd, 1H, J 2.7, 8.8 Hz), 7.47-7.33 (m, 5H), 6.92 (d, 1H, J 8.8 Hz), 6.87-6.84 (m, 3H), 5.13 (dd, 1H, J 2.2, 10.1 Hz), 4.04-3.96 (m, 2H), 2.99-2.91 (m, 1H), 2.81-2.69 (m, 3H), 2.20-2.12 (m, 2H), 2.08-1.98 (m, 1H), 1.79-1.74 (m, 3H), 1.50-1.35 (m, 11H).

Workup

  1. temperatureThe mixture was refluxed for few hours
  2. customReaction
  3. customwas quenched with addition of water
  4. extractionextracted with ethyl acetate
  5. washCombined organic layers were washed with water, saturated sodium carbonate solution
  6. dry with materialdried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-3493b9f78d744d1d929c3a78034faaf1
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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