6-Hydroxybuspirone → Buspirone

HRID 2182753Notes

Reaction equation

HRID 2182753 reaction equation
[CH:1]1[CH:2]=[N:3][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:27](=[O:28])[CH:26]([OH:29])[C:21]4([CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:20][C:18]3=[O:19])[CH2:9][CH2:8]2)=[N:5][CH:6]=1>O>[CH:1]1[CH:6]=[N:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:27](=[O:28])[CH:26]([OH:29])[C:21]4([CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:20][C:18]3=[O:19])[CH2:11][CH2:12]2)=[N:3][CH:2]=1.[CH:1]1[CH:6]=[N:5][C:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:27](=[O:28])[CH2:26][C:21]4([CH2:22][CH2:23][CH2:24][CH2:25]4)[CH2:20][C:18]3=[O:19])[CH2:9][CH2:8]2)=[N:3][CH:2]=1

Participants

4

Reactant 1

HCID 99309136-Hydroxybuspirone

Product 2

HCID 2477BuspironeHCID 99309136-Hydroxybuspirone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Batch A. Approximately 1000 mL was transferred to a vessel equipped with a magnetic stirrer and water was added (15 mL, Karl Fischer titration indicated 3.94% water). This solution was then slowly cooled to ambient temperature while stirring, and seeded with 6-hydroxybuspirone (approximately 20 mg). The mixture was filtered seven days later on a 4-6 micron glass sintered filter and the mother liquor saved for analysis (740 mL). The off-white solid was subsequently washed with IPA (2×260 mL). The white solid was suctioned dried for 1 h and then placed into a an oven at 45° C. (27 in Hg with an N2 bleed for 69 h). 6-Hydroxybuspirone was obtained as an off-white solid (166.0 g, purity=99 AP, buspirone AP=0.35, and a trans-diol side product AP=0.54).

Workup

  1. customApproximately 1000 mL was transferred to a vessel
  2. customequipped with a magnetic stirrer
  3. filtrationThe mixture was filtered seven days later on a 4-6 micron glass
  4. filtrationsintered filter
  5. washThe off-white solid was subsequently washed with IPA (2×260 mL)
  6. customThe white solid was suctioned dried for 1 h
  7. customplaced into a an oven at 45° C.

Sources & evidence

ORD record
ord-c6c2130c098f4fd3a8e45249ec53aae5
Source dataset
uspto-grants-2005_05
Patent number
US06897309B2

Reaction notes

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