1-(p-Methoxyphenyl)-2-propanone → HCID 18352986, compound

HRID 429826Notes

Reaction equation

HRID 429826 reaction equation
C([BH3-])#N.[Na+].[NH2:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](=O)[CH3:30])=[CH:24][CH:23]=1>CO>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([NH:5][CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH3:30])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 18352986HCID 18352986, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium cyanoborohydride (1.07 grams, 17 mmole), 4-aminomethyl-1-(tert-butoxycarbonyl)piperidine (3.0 grams, 14.3 mole) and 1-(4-methoxyphenyl)propan-2-one (2.35 grams, 14.31 mmole) in methanol (50 ml) was stirred at 22° C. for 17 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The dried (anhydrous magnesium sulfate) organic phase was concentrated under reduced pressure to leave N-[2-(4-methoxyphenyl)-1-methylethyl]-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine as an oil (4.28 grams, 82%); hydrochloride, m.p. 198-199° C. (methanol/ethyl ether), M+H 391.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe dried (anhydrous magnesium sulfate) organic phase
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-a0520b2b631b4525a2c7b2edd19a4a5f
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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