Acetic Acid → HCID 18321485, compound

HRID 1782716Notes

Reaction equation

HRID 1782716 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:6])[CH3:3].[C:14]1([CH2:20][N:21]2[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:3][C:2]([CH3:13])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([CH:24]2[CH2:23][CH2:22][N:21]([CH2:20][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:26][CH2:25]2)[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 192201-Benzyl-4-piperidoneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18321485HCID 18321485, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 15.0 g ( 0.8054 mol) of 1-(1,1-dimethylethoxycarbonyl)piperazine and 14.26 ml (0.08053 mol) of 1-(phenylmethyl)-4-piperidinone in 250 ml of methanol was adjusted to a pH of between 5 and 6 by dropwise addition of acetic acid and mixed in batches with a total of 4.13 g ( 0.0624 mol) of 95% sodium cyanoborohydride, whilst taking care to maintain a pH of 5 to 6 by further dropwise addition of acetic acid. After stirring for 18 hours at room temperature the mixture was evaporated down in vacuo, the residue was made alkaline with soda and divided between water and ethyl acetate. After working up the ethyl acetate phase in the usual way 21.76 g (75.2% of theory) of a highly viscous colourless oil were obtained, Rf 0.66 (FM1).

Workup

  1. temperatureto maintain a pH of 5 to 6
  2. customwas evaporated down in vacuo
  3. customwere obtained

Sources & evidence

ORD record
ord-e0a39eff4aed4211888dcddb714a3e82
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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