Acetaldehyde → HCID 66938866, compound

HRID 1716894Notes

Reaction equation

HRID 1716894 reaction equation
[CH:1](=O)[CH3:2].[CH3:4][N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2F)[CH2:7][CH2:6]1.C([BH3-])#N.[Na+].[F:24]C(F)(F)C(O)=O>CO>[CH3:4][N:5]1[CH2:6][CH2:7][CH:8]([NH:11][CH2:12][CH2:17][C:16]2[CH:2]=[CH:1][CH:13]=[C:14]([Cl:18])[C:15]=2[F:24])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 6422Trifluoroacetic acidHCID 5003444Sodium cyanoborohydrideHCID 43123011HCID 43123011, compound

Product 1

HCID 66938866HCID 66938866, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Add acetaldehyde (0.817 g) to a solution of 1-methyl-4-(3-chloro-2-fluorophenylamino)piperidine (Preparation 19) (0.45 g), sodium cyanoborohydride (0.123 g) and trifluoroacetic acid (0.633 g) in methanol (20 mL) and heat in a sealed tube at 80° C. for three days. Load on a SCX column (10 g), wash with methanol, elute with 2M NH3 in methanol, evaporate, and further purify on a silica gel column (35 g), using a gradient of dichloromethane-2M NH3 in methanol to give 0.50 g of the title intermediate as a colorless oil: mass spectrum (electric spray) m/z=271 (M+1); 1H NMR (CDCl3): 6.94 (m, 3H), 3.14 (q, J=7.0 Hz, 2H), 3.06 (m, 1H), 2.84 (br d, 2H), 2.22 (s, 3H), 1.93 (m, 2H), 1.74 (m, 4H), 0.95 (t, J=7.0 Hz, 3H).

Workup

  1. washLoad on a SCX column (10 g), wash with methanol
  2. washelute with 2M NH3 in methanol
  3. customevaporate
  4. customfurther purify on a silica gel column (35 g)

Sources & evidence

ORD record
ord-c117170e37644e86a29110da30af2e58
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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