Triethylamine → HCID 14536422, compound

HRID 1607881Notes

Reaction equation

HRID 1607881 reaction equation
[CH:1]1([NH2:16])[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:24](Cl)(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[C:24]([NH:16][CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[NH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:4][CH2:3][CH2:2]1)(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67340Hexanoyl chlorideHCID 14536421HCID 14536421, compound

Product 1

HCID 14536422HCID 14536422, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled solution of 1,2,3,4-tetrahydro-1,9-acridinediamine (4.96 g) and triethylamine (3.6 ml) in 100 ml of tetrahydrofuran was added hexanoylchloride (3.6 ml). This was stirred for five minutes, then quenched into adilute NaOH solution. The aqueous phase was extracted with ethyl acetate (3x) and dried (MgSO4). The organics were concentrated to a semi-solid which was triturated with ethyl ether to give 3.32 g of a pale yellow powder, m.p. 205°-211° C. (dec.). This was recrystallized from methanol/water to give 2.54 g of a pale yellow powder,m.p. 214°-217° (dec.).

Workup

  1. customquenched into adilute NaOH solution
  2. extractionThe aqueous phase was extracted with ethyl acetate (3x)
  3. dry with materialdried (MgSO4)
  4. concentrationThe organics were concentrated to a semi-solid which
  5. customwas triturated with ethyl ether

Sources & evidence

ORD record
ord-7653d0ed94a44728a0c3eb511bc88b00
Source dataset
uspto-grants-1989_09
Patent number
US04868177

Reaction notes

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