Triethylamine → HCID 54468521, compound

HRID 1954784Notes

Reaction equation

HRID 1954784 reaction equation
[NH2:1][C@@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C(N(CC)CC)C.[C:26](Cl)(=[O:30])[CH2:27][CH2:28][CH3:29]>C(Cl)Cl>[CH3:18][N:15]1[CH2:16][CH2:17][N:12]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[CH2:3][C@H:2]([NH:1][C:26](=[O:30])[CH2:27][CH2:28][CH3:29])[CH2:11][CH2:10]3)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 54468521HCID 54468521, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene (300 mg, 1.2 mmol) and triethylamine (260 μL, 1.8 mmol) in methylene chloride (50 mL) was added dropwise butyryl chloride (140 μL, 1.3 mmol) in methylene chloride (10 mL). After the addition the reaction was allowed to stir at ambient temperature for 1 h and then washed with a dilute aqueous sodium hydrogen carbonate solution. The phases were separated and the combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo to give a crude product which was purified on a silica gel column using chloroform/methanol/concentrated ammonium hydroxide (95:4:0.5) as the eluent. Yield: 330 mg (86%) of the title compound as white crystals: mp 131-132° C.; [α]21D +24° (c 0.50, chloroform); EIMS (70 eV) m/z (relative intensity) 315 (39, M+).

Workup

  1. additionAfter the addition the reaction
  2. washwashed with a dilute aqueous sodium hydrogen carbonate solution
  3. customThe phases were separated
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6b1e71a67a10472084e84f82c1812d84
Source dataset
uspto-grants-2000_09
Patent number
US06124283

Reaction notes

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