Triethylamine → Cyclohexanecarboxylic acid [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amide

HRID 1827525Notes

Reaction equation

HRID 1827525 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)=[CH:19][CH:18]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH:37]1([C:43](Cl)=[O:44])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1>C(Cl)Cl>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][O:25]4)=[CH:19][CH:18]=3)[C:43]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[O:44])=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 22137309[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine

Product 1

HCID 86592784Cyclohexanecarboxylic acid [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-benzyl]-amine (1.70 g, 4.29 mmol) and triethylamine (2.40 mL, 17.2 mmol) in methylene chloride (8–10 mL) at 0° C. was added cyclohexanecarbonyl chloride (1.72 mL, 12.87 mmol) in methylene chloride (30 mL) dropwise. The reaction mixture was stirred for 1 hr. and was quenched with water/saturated sodium bicarbonate (1/1, 40–50 mL). The layers were separated and the aqueous solution was washed with methylene chloride (2×25 mL). The combined organic solutions were dried (magnesium sulfate), filtered, and concentrated. Medium pressure chromatography using a solvent gradient (methylene chloride to 10% methanol/methylene chloride) afforded the title compound of Step A. MS 507 (M+1)+

Workup

  1. customand was quenched with water/saturated sodium bicarbonate (1/1, 40–50 mL)
  2. customThe layers were separated
  3. washthe aqueous solution was washed with methylene chloride (2×25 mL)
  4. dry with materialThe combined organic solutions were dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a8a357a2fcd64a188b56c15d7bf0de03
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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