Diethylamine → HCID 11287680, compound

HRID 2228462Notes

Reaction equation

HRID 2228462 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(O)C.[CH2:15]([NH:17]CC)C.[CH3:20][CH2:21][CH2:22][CH2:23]CC.C(O)C>>[CH:8]1([N:3]2[CH2:4][CH2:5][CH2:15][NH:17][CH2:2][CH2:1]2)[C:7]2[C:20](=[CH:21][CH:22]=[CH:23][CH:6]=2)[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 8021DiethylamineHCID 21879635Ethanol hexaneHCID 21881120Hexane ethanol diethylamine

Product 1

HCID 11287680HCID 11287680, compound

Procedure

R(−) N-(1,2,3,4-tetrahydro-1-naphthalenyl)homopiperazine was obtained as the second material to elute on subjecting racemic material (5.3 g), prepared as in Example 2, to preparative Chiral Pak AD HPLC resolution using a hexane/ethanol mixture with modification with diethylamine. The enantiomeric purity was determined on an analytical scale using hexane:ethanol:diethylamine (90:5:.05, v/v) and detection at 220 nm. The solution containing this enantiomer was concentrated using a rotary evaporator to give the title compound (2.65 g), [α]D22−94° (c=0.64, methanol); 98.5% ee.

Workup

  1. washto elute
  2. custommaterial (5.3 g), prepared as in Example 2
  3. additionThe solution containing this enantiomer
  4. concentrationwas concentrated
  5. customa rotary evaporator

Sources & evidence

ORD record
ord-57aa50f948cf4bfabfe8a0ce42a1839f
Source dataset
uspto-grants-2002_07
Patent number
US06417183B1

Reaction notes

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