Acetic Acid → HCID 18469935, compound

HRID 2228463Notes

Reaction equation

HRID 2228463 reaction equation
[CH:1]1([N:11]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:18][C:19]([CH3:21])=O.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1.CO.C(Cl)(Cl)Cl>[CH:19]([N:14]1[CH2:15][CH2:16][CH2:17][N:11]([CH:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)[CH2:12][CH2:13]1)([CH3:21])[CH3:18]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 11287680HCID 11287680, compound

Product 1

HCID 18469935HCID 18469935, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 100 ml 3-necked flask under nitrogen atmosphere was charged sequentially with N-(1,2,3,4-tetrahydro-1-naphthalenyl)homopiperazine (0.73 g; 3.2 mmol) in THF (20 ml), methanol (10 ml) and acetone (3.3 ml; 45 mmol). To this stirred solution, sodium cyanoborohydride (0.30 g; 4.75 mmol) was added as a solid followed by acetic acid (0.24 ml; 4.2 mmol). After stirring at ambient temperature for 45 minutes, tlc analysis (silica gel, 9:1 CHCl3:CH3OH) of an aliquot revealed the absence of starting amine (Rf 0.03) and the presence of a major component with Rf 0.16. The content of the flask was then concentrated in vacuo. The residue was treated with aqueous sodium bicarbonate and extracted several times with ethyl acetate which was then dried with sodium sulphate. Filtration and removal of solvent in vacuo gave an oil which was subjected to high vacuum for four hours at ambient temperature to yield the title compound (0.87 g); tlc (ibid), homogeneous, Rf 0.16; 1H nmr δ 1.01-1.05 (6H), 3.88-3.92 (m, 1H), 6.98-7.22 (m, 3H), 7.77-7.79 (1, H). Anal: Calcd. for C18H28N2; C, 79.36; H, 10.36; N, 10.28. Found: C, 79.46; H, 10.12; N, 10.08.

Workup

  1. concentrationThe content of the flask was then concentrated in vacuo
  2. additionThe residue was treated with aqueous sodium bicarbonate
  3. extractionextracted several times with ethyl acetate which
  4. dry with materialwas then dried with sodium sulphate
  5. filtrationFiltration and removal of solvent in vacuo
  6. customgave an oil which
  7. waitwas subjected to high vacuum for four hours at ambient temperature

Sources & evidence

ORD record
ord-a6069685273f46518e6908f86f034b7a
Source dataset
uspto-grants-2002_07
Patent number
US06417183B1

Reaction notes

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