Phthalic Anhydride → HCID 58786650, compound

HRID 1376028Notes

Reaction equation

HRID 1376028 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]1(=O)[O:29][C:27](=[O:28])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH2:15][N:16]2[C:27](=[O:28])[C:26]3[C:25](=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:24]2=[O:29])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 6811Phthalic AnhydrideHCID 58780687HCID 58780687, compound

Product 1

HCID 58786650HCID 58786650, compoundYield 95%

Conditions

Temperature
130 °C

Procedure

To 4-2[-amino-1-(2-chloro-phenyl)-ethyl]-1-Boc-piperazine (201) (4.34g, 12.7 mmol) was added phthalic anhydride (1.89 g, 12.7 mmol). The mixture was heated at 130° C. for 1 h and then allowed to cool to room temperature. The resulting solid was recrystallized from MeOH. The enantiomers of the phthalimide-protected product were separated by chiral chromatography, using a Chiralcel OD (4.6×250 mm) column, eluting with 5% 3A alcohol in heptane at 1 mL/min. The first eluting isomer was labeled isomer #1 and the second eluting isomer #2. 5.6 g (95%) of the mixture was isolated and separated.

Workup

  1. temperatureto cool to room temperature
  2. customThe resulting solid was recrystallized from MeOH
  3. customThe enantiomers of the phthalimide-protected product were separated by chiral chromatography
  4. washeluting with 5% 3A alcohol in heptane at 1 mL/min

Sources & evidence

ORD record
ord-950cb8f9322442fea851ea77c59be83b
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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