Morpholine → tert-butyl (3RS,4RS)-4-[4-(3-morpholin-4-yl-propoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

HRID 1858673Notes

Reaction equation

HRID 1858673 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O-:24])=[O:23])[CH2:18][CH:17]2[O:25][CH2:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=2)=[CH:12][CH:11]=1)(=O)=O.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>C(OCC)(=O)C>[N:37]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:13]([CH3:16])([CH3:14])[CH3:12])=[O:23])[CH2:18][CH:17]3[O:25][CH2:26][C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)=[CH:12][CH:11]=2)[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 22127056HCID 22127056, compound

Product 1

HCID 54346012tert-butyl (3RS,4RS)-4-[4-(3-morpholin-4-yl-propoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 200 mg (0.35 mmol) of tert-butyl 3RS,4RS)-4-[4-(3-methylsulphonyloxy-propoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate in 1 ml of ethyl acetate was treated with 60 μl of morpholine and boiled under reflux for 3 hours. Subsequently, the reaction solution was diluted with 5 ml of ethyl acetate and extracted twice with 1 ml of saturated sodium hydrogen carbonate solution each time. The organic phases were dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The colourless oil (169 mg) was chromatographed on silica gel using ethyl acetate and the eluent. There were obtained 142 mg of tert-butyl (3RS,4RS)-4-[4-(3-morpholin-4-yl-propoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate in the form of white crystals; MS: 561 (M+H)+.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionextracted twice with 1 ml of saturated sodium hydrogen carbonate solution each time
  3. dry with materialThe organic phases were dried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customdried in a high vacuum
  6. customThe colourless oil (169 mg) was chromatographed on silica gel

Sources & evidence

ORD record
ord-29778778ae9a43048037a97215a49958
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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