Triethylamine → HCID 19023665, compound

HRID 2255439Notes

Reaction equation

HRID 2255439 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=O.C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.[O:29]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH:32]([CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][CH:44]([NH2:47])[CH2:43][CH2:42]2)[CH2:31][CH2:30]1>C(Cl)Cl>[O:29]1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[CH:32]([CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][CH:44]([NH:47][C:11]([CH:2]3[CH2:3][CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:1]3)=[O:13])[CH2:43][CH2:42]2)[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acidHCID 86166943HCID 86166943, compound

Product 1

HCID 19023665HCID 19023665, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (176 mg, 1 mmol) and triethylamine (0.25 ml) in methylene chloride (5 ml), isobutylchloroformate (136 mg, 1 mmol) was added. After 5 minutes N-[1-[2-(3,4-dihydro-2H-1-benzopyran-4-yl)ethyl]-4-aminopiperidine (260 mg, 1 mmol) in methylene chloride was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was quenched with 2N potassium hydroxide solution. The organic layer was separated, washed with distilled water and dried (Na2SO4). Evaporation of the solvent gave a white solid which was crystallized from diethyl ether to afford the title compound (140 mg, 33%), m.p.=130-2°, Anal C27H34N2O2.0.25 H2O, Calc, C, 76.65; H, 8.22, N, 6.62; Found C,76.34; H, 8.32; N, 6.59.

Workup

  1. customThe reaction mixture was quenched with 2N potassium hydroxide solution
  2. customThe organic layer was separated
  3. washwashed with distilled water
  4. dry with materialdried (Na2SO4)
  5. customEvaporation of the solvent
  6. customgave a white solid which
  7. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-54aa6bc657cd4f61bfdb2af99a42562d
Source dataset
uspto-grants-1993_08
Patent number
US05240943

Reaction notes

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