Sodium Hydroxide → HCID 68071663, compound

HRID 1519556Notes

Reaction equation

HRID 1519556 reaction equation
[N:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([C:17]#[N:18])[CH:11]=[CH:10][C:9]=3[CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C.C(Cl)Cl>[N+:28]([C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][N:4]2[CH2:3][CH2:2][N:1]([CH:7]3[CH2:16][CH2:15][C:14]4[CH:13]=[C:12]([C:17]#[N:18])[CH:11]=[CH:10][C:9]=4[CH2:8]3)[CH2:6][CH2:5]2)=[CH:23][CH:24]=1)([O-:30])=[O:29]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 792664-Nitrophenethyl bromideHCID 81531DiisopropylethylamineHCID 67514156HCID 67514156, compound

Product 1

HCID 68071663HCID 68071663, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-piperazin-1-yl-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (generated from treateding tert-Butyl 4-(6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl) piperazine-1-carboxylate (110 mg, 0.32 mmol) with trifluoroacetic acid (2 ml, 26 mmol) at RT), 1-(2-bromoethyl)-4-nitrobenzene (47 mg, 0.21 mmol), and Hunig's Base (0.054 ml, 0.31 mmol in 1 ml DMF was stirred at 60° C. for 21 hours. The reaction was shaken with 1 ml 1 N NaOH and 1 mL DCM. The organic layer was separated and evaporated to dryness. The residue was purified by mass directed HPLC to yield 6-{4-[2-(4-nitrophenyl)ethyl]piperazin-1yl}-5,6,7,8-tetrahydronaphthalene-2-carbonitrile. LC-MS (IE, m/z): 391 [M+1]+. (0.050 μM)

Workup

  1. customThe organic layer was separated
  2. customevaporated to dryness
  3. customThe residue was purified by mass

Sources & evidence

ORD record
ord-26031c90440b42fa80f7ef95f7414b78
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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