Water → Ammonium Hydroxide

HRID 1584751Notes

Reaction equation

HRID 1584751 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:14](=O)[CH2:13][CH2:12][CH2:11]2.[CH:19]1(N2CCNCC2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[BH3-][C:32]#[N:33].[Na+].O>C(Cl)Cl>[NH4+:1].[OH-:7].[CH:19]1([CH:11]2[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([O:7][C:2]4[N:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH:9]=3)[CH:14]([N:33]3[CH2:32][CH2:2][NH:1][CH2:6][CH2:5]3)[CH2:13][CH2:12]2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 962WaterHCID 872981-CyclohexylpiperazineHCID 5003444Sodium cyanoborohydrideHCID 15458150HCID 15458150, compound

Product 2

HCID 14923Ammonium HydroxideHCID 70135975HCID 70135975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-[(2-Pyrimidinyl)oxy]-tetralone (3.2 mmol), N-cyclohexylpiperazine (3.2 mmol) and Ti(O-2-Pr)4 (3.2 mmol) were dissolved in CH2Cl2 (10 mL). The solution was stirred at room temperature for 20 hours and then quenched with NaCNBH3 (6.4 mmol in 5 mL EtOH). Water (20 mL) was added, the resulting mixture was filtered through a pad of `Celite`, and the residue was rinsed with CH2Cl2 (10 mL). The organic layer was dried with Na2SO4 and evaporated to yield the crude product as an oil. Purification by column chromatography on TLC-grade silica gel and 100:3:1 CH2Cl2 :EtOH:NH4OH as eluant gave the pure product, 4-cyclohexyl-1-piperazinyl-[6-[(2-pyrimidinyl)oxy]]-1,2,3,4-tetrahydro-naphthalene. This was converted to the dimaleate salt, m.p. 179-181.5° C., by dissolving in EtOAc and heating with 2 equivalents of maleic acid.

Workup

  1. filtrationthe resulting mixture was filtered through a pad of `Celite`, and the residue
  2. washwas rinsed with CH2Cl2 (10 mL)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. customevaporated
  5. customto yield the crude product as an oil
  6. customPurification by column chromatography on TLC-grade silica gel and 100:3:1 CH2Cl2

Sources & evidence

ORD record
ord-a26baa1c0a9e4f79baf462eaac0fb0f4
Source dataset
uspto-grants-1999_08
Patent number
US05935958

Reaction notes

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