Acetic Acid → HCID 66711527, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[C:21](O)(=O)C.C(Cl)Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([N:15]2[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Procedure
3-Oxo-piperidine-1-carboxylic acid tert-butyl ester (2.0 g, 1.0E1 mmol) and piperazine, 1-methyl- (1.10 g, 11.0 mmol) were dissolved in a solution of Acetic acid (0.500 mL, 8.79 mmol) and Methylene chloride (50.0 mL, 7.80E2 mmol). After stirring at room temperature for 15 minutes, Sodium triacetoxyborohydride (4.2 g, 2.0E1 mmol) was added and the reaction was allowed to stir overnight at room temperature. The reaction mixture was poured over saturated sodium bicarbonate and organics were extracted with dichloromethane/ethyl acetate. Combined extracts were then dried over sodium sulfate, filtered and reduced. TLC showed evidence of a new product (iodine visualization). 2.25 g of crude 3-(4-Methyl-piperazin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester was used without further purification.
Workup
- stirringto stir overnight at room temperature
- extractionorganics were extracted with dichloromethane/ethyl acetate
- dry with materialCombined extracts were then dried over sodium sulfate
- filtrationfiltered
- custom2.25 g of crude 3-(4-Methyl-piperazin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester was used without further purification
Sources & evidence
- ORD record
- ord-270bc7733e304d5b96ad3d0183166a3c
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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