Cyclopropylamine → HCID 66783991, compound

HRID 1095823Notes

Reaction equation

HRID 1095823 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:22][CH2:21][C:18]3([O:20][CH2:19]3)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>CO.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:16][CH2:17][C:18]([CH2:19][NH:26][CH:23]3[CH2:25][CH2:24]3)([OH:20])[CH2:21][CH2:22]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 86630596HCID 86630596, compound

Product 1

HCID 66783991HCID 66783991, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-[4-(benzyloxy)phenyl]-1-oxa-6-azaspiro[2,5]octane (500 mg, 1.69 mmol) and cyclopropylamine (195 mg, 3.38 mmol) were mixed in methanol, and heated overnight under reflux. The reaction solution was diluted with ethyl acetate, washed with water and saturated saline in that order, and the organic layer was dried with sodium sulfate. The solvent was evaporated off under reduced pressure to obtain a crude product. The resulting crude product was purified through silica gel column chromatography (eluate: methanol/chloroform=1/99 to 6/94) to obtain the entitled compound (511 mg, 85%) as a yellow solid.

Workup

  1. temperatureheated overnight
  2. temperatureunder reflux
  3. washwashed with water and saturated saline in that order
  4. dry with materialthe organic layer was dried with sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customto obtain a crude product
  7. customThe resulting crude product was purified through silica gel column chromatography (eluate: methanol/chloroform=1/99 to 6/94)

Sources & evidence

ORD record
ord-c7f4fc09c054441fad3cf20acc23d7be
Source dataset
uspto-grants-2012_03
Patent number
US08138206B2

Reaction notes

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