Acetic Acid → HCID 18919856, compound

HRID 1291103Notes

Reaction equation

HRID 1291103 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([O:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][CH2:8]1)=[O:5].C=O.[BH3-][C:27]#N.[Na+].C(O)(=O)C>C(#N)C.CCOCC.O>[CH3:27][NH:1][C:2]1[CH:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([O:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][CH2:12]1)=[O:5]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 712Formaldehyde2×HCID 5003444Sodium cyanoborohydride2×HCID 18919823HCID 18919823, compound

Product 1

HCID 18919856HCID 18919856, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584184Diethylether waterSolvent

Procedure

0.2 g (0.00064 mol) of 1-benzyl-piperidin-4-yl 2-amino-benzoate was dissolved in 10 ml of acetonitrile and treated with 0.5 ml (0.0064 mol) of formaldehyde (37%) and 0.24 g (0.0032 mol) of NaBH3CN. The pH was adjusted to 6 by the addition of glacial acetic acid. The mixture was stirred at room temperature for 12 hrs., a further 0.15 g of NaBH3CN and 0.2 ml of formaldehyde were then. added and the pH was again adjusted to 6 by means of glacial acetic acid. After stirring for a further 2 hrs. the mixture was taken up in 100 ml of ether/water (1:1) and the organic phase was washed twice with saturated bicarbonate solution and once with saturated sodium chloride solution and dried over MgSO4. The residue was chromatographed on silica gel with dichloromethanelmethanol (39:1) as the eluent. 0.128 g (61%) of 1-benzyl-piperidin-4-yl 2-methylamino-benzoate was obtained as a colorless oil. MS: me/e=325 (C20H25N2O2 +).

Workup

  1. additionadded
  2. stirringAfter stirring for a further 2 hrs
  3. washthe organic phase was washed twice with saturated bicarbonate solution and once with saturated sodium chloride solution
  4. dry with materialdried over MgSO4
  5. customThe residue was chromatographed on silica gel with dichloromethanelmethanol (39:1) as the eluent

Sources & evidence

ORD record
ord-414c61b4978845b887e964fa3bb7b3b7
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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