Triethylamine → ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate

HRID 2416576Notes

Reaction equation

HRID 2416576 reaction equation
N[C:2]1[C:11]2C(=CC=C(OCCNC(=O)OC(C)(C)C)C=2)C=CN=1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([O:36][C:37]2[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>Cl.O1CCOCC1.ClCCl>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([O:36][C:37]2[CH:38]=[CH:39][C:40]([C:41]([O:43][CH2:2][CH3:11])=[O:42])=[CH:44][CH:45]=2)[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27946494-{[1-(tert-Butoxycarbonyl)piperidin-4-yl]oxy}benzoic acidHCID 22631368HCID 22631368, compound

Product 1

HCID 11783050ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent4×

Procedure

648 mg (2.15 mmol) of t-butyl [2-(1-aminoisoquinoline-7-yloxy)ethyl]carbamate was dissolved in a mixture of 2.5 ml of 4 N solution of hydrogen chloride in dioxane and 5 ml of dioxane. The obtained solution was stirred at room temperature overnight. The solvent was evaporated, and the residue was dissolved in 10 ml of DMF. 752 mg (2.36 mmol) of 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoic acid, 451 mg (2.36 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 319 mg (2.36 mmol) of 1-hydroxybenzotriazole and 0.99 ml (7.08 mmol) of triethylamine were added to the obtained solution, and they were stirred at room temperature overnight. The reaction mixture was treated with dichloromethane as the extracting solvent in an ordinary manner, and the obtained crude product was dissolved in a mixture of 2 ml of 4 N solution of hydrogen chloride in dioxane and 1 ml of dioxane. The obtained solution was stirred at room temperature overnight. The title compound was obtained in the same manner as that in step 4 in Example 1.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in 10 ml of DMF
  3. stirringwere stirred at room temperature overnight
  4. customthe obtained crude product
  5. stirringThe obtained solution was stirred at room temperature overnight

Sources & evidence

ORD record
ord-b45417fad2204055975a0ff3c8c0ac21
Source dataset
uspto-grants-2004_11
Patent number
US06825181B1

Reaction notes

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