Acetic Acid → HCID 18469935, compound

HRID 2228467Notes

Reaction equation

HRID 2228467 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([N:11]2[CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:3][CH2:2]1.[CH3:18][C:19]([CH3:21])=O.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1.CO>[CH:19]([N:14]1[CH2:15][CH2:16][CH2:17][N:11]([CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1][CH2:2][CH2:3]2)[CH2:12][CH2:13]1)([CH3:21])[CH3:18]

Participants

7

Reactant 4

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

Product 1

HCID 18469935HCID 18469935, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

R(−) N-(1,2,3,4-tetrahydronaphthalen4-yl)homopiperazine (2.00 g; 8.7 mmol) in THF (50 ml), methanol (25 ml) and acetone (15.5 ml; 174 mmol) was reacted with sodium cyanoborohydride (1.1 g; 17.6 mmol) and acetic acid (1.0 ml) as in Example 14. Kugelrohr distillation gave the title compound (2.29 g), bp (air bath temperature) 165-175° C. at 180 mtorr; [α]D22−74° (c=0.64, methanol).

Workup

  1. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-d01c7aedd02140e1ab6d3a34c74c3bfa
Source dataset
uspto-grants-2002_07
Patent number
US06417183B1

Reaction notes

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