Triethylamine → HCID 178420462, compound

HRID 893331Notes

Reaction equation

HRID 893331 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][CH:13]([C:16](O)=O)[CH2:12][CH2:11]2)=[CH:2]1.C(N(CC)CC)C.ClC(OCC(C)C)=O.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[N:40]1[CH2:41][CH2:42][N:43]([CH2:16][C@H:13]2[CH2:14][CH2:15][C@H:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:11][CH2:12]2)[CH2:44][CH2:45]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 944591-(2-Pyridyl)piperazineHCID 516892Sodium BicarbonateHCID 19892081HCID 19892081, compound

Product 1

HCID 178420462HCID 178420462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(1H-3-indolyl)-cyclohexanecarboxylic acid (1.60 g, 6.57 mmol) and methylene chloride (30 mL) is treated with triethylamine (1.53 mL, 10.97 mmol) and the resulting solution is cooled to 0° C. Isobutyl chloroformate (0.93 mL, 7.15 mmol) is added and the reaction is stirred at 0° C. for 10 minutes. A solution of 1-(2-pyridinyl)piperazine (1.18 g, 7.23 mmol) in methylene chloride is added and the reaction is then stirred at ambient temperature for 18 hours. A saturated solution of sodium bicarbonate (20 mL) is added and the organic phase is separated. The aqueous phase is extracted with two 40 mL portions of methylene chloride and the combined organic extracts are dried with sodium sulfate, and evaporated. The residue is chromatographed on silica gel (2% methanol in chloroform) and 2 main fractions are isolated. The first fraction consisted of trans 1-({4-[1H-3-indolyl]cyclohexyl}carboxyl)-4-(2-pyridinyl)piperazine and the second fraction consisted of the corresponding cis isomer. The resulting trans amide is reduced by the method described in Example 1 to give trans 3-[4-[4-(2-pyridinyl)-1-piperazinylmethyl]cyclohexyl]-1H-indole (Example 15); m/e 374.

Workup

  1. stirringthe reaction is then stirred at ambient temperature for 18 hours
  2. customthe organic phase is separated
  3. extractionThe aqueous phase is extracted with two 40 mL portions of methylene chloride
  4. dry with materialthe combined organic extracts are dried with sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel (2% methanol in chloroform) and 2 main fractions
  7. customare isolated

Sources & evidence

ORD record
ord-2a87cdcece89441585b44308266570b9
Source dataset
uspto-grants-1992_06
Patent number
US05124332

Reaction notes

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