Ammonia → CBz-D-phenylglycine 4-(1-methylpiperidin-4-yl)piperidinamide

HRID 1384891Notes

Reaction equation

HRID 1384891 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([NH:11][C@@H:12]([C:19]([OH:21])=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:3][CH:2]=1.[C:22]([N:29]1[CH2:34][CH2:33][CH:32]([CH:35]2[CH2:40][CH2:39][N:38]([C:41]([NH2:43])=[O:42])[CH2:37][CH2:36]2)[CH2:31][CH2:30]1)(OC(C)(C)C)=O.C([BH3-])#N.[Na+].N>C(#N)C.C=O>[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([NH:11][C@@H:12]([C:19]([OH:21])=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])=[CH:3][CH:2]=1.[CH3:22][N:29]1[CH2:30][CH2:31][CH:32]([CH:35]2[CH2:40][CH2:39][N:38]([C:41]([NH2:43])=[O:42])[CH2:37][CH2:36]2)[CH2:33][CH2:34]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 5003444Sodium cyanoborohydrideHCID 131722771CBz-D-phenylglycine 4-[l-(Boc)piperidin-4-yl]piperidinamide

Product 1

HCID 131722772CBz-D-phenylglycine 4-(1-methylpiperidin-4-yl)piperidinamideYield 97%

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of CBz-D-phenylglycine-4-[1-(Boc)piperidin-4-yl]piperidinamide (1.1 g, 2.5 mmol) in acetonitrile (40 ml) and aq. formaldehyde (10 ml) was added sodium cyanoborohydride (315 mg, 5 mmol) portionwise over 10 min. The reaction mixture was left to stir for 3 hours and then poured onto water (50 ml), containing conc ammonia solution (5 ml) and left to stir for 15 min. Extraction with ethyl acetate (100 ml), washing with brine and drying gave the title compound as a colourless oil (1.1 g, 97%).

Workup

  1. waitThe reaction mixture was left
  2. additionpoured onto water (50 ml)
  3. waitleft
  4. stirringto stir for 15 min
  5. extractionExtraction with ethyl acetate (100 ml)
  6. washwashing with brine
  7. customdrying

Sources & evidence

ORD record
ord-03d5a1bf5b2c4f249a7faa778fcaca45
Source dataset
uspto-grants-2001_07
Patent number
US06262069B1

Reaction notes

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