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Water → HCID 19360594, compound

HRID 376976
Notes
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Reaction equation

HRID 376976 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[CH2:4][CH2:5][OH:6].[CH2:8]([C:15]([N:30]([CH3:32])[CH3:31])([CH2:28][CH3:29])[C:16]([C:18]1[CH:23]=[CH:22][C:21](OC)=[C:20]([O:26][CH3:27])[CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CC(N(C)C)=O>[CH2:8]([C:15]([N:30]([CH3:31])[CH3:32])([CH2:28][CH3:29])[C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:6][CH2:5][CH2:4][CH2:3][OH:7])=[C:20]([O:26][CH3:27])[CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 104421,3-PropanediolHCID 24758Sodium hydrideHCID 221842401-Butanone, 1-(3,4-dimethoxyphenyl)-2-(dimethylamino)-2-(phenylmethyl)-

Product 1

HCID 19360594HCID 19360594, compound

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent
2×

Conditions

Temperature
120 °C

Procedure

0.40 mol of sodium hydride are suspended in 500 ml of dry dimethylacetamide and 72.3 ml (1.0 mol) of 1,3-propanediol are added dropwise at 0° C. Then 68.3 g (0.20 mol) of 2-benzyl-1-(3,4-dimethoxy-phenyl)-2-dimethylamino-butan-1-one in dimethylacetamide are added dropwise at 0° C. After the solution is stirred at 120° C. for 18 h, the solution is poured into water. The crude product is extracted with ethyl acetate, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (40:60) as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 0.69 (t, 3H), 1.83-1.92 (m, 1H), 2.04-2.16 (m, 3H), 2.38 (s, 6H), 2.40-2.55 (bs, 1H), 3.18-3.23 (m, 2H), 3.88 (s, 3H), 3.89 (t, 2H), 4.27 (t, 2H), 6.84 (d, 1H), 7.15-7.28 (m, 5H), 7.93 (d, 1H), 8.20 (dd, 1H).

Workup

  1. extractionThe crude product is extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (40:60) as an eluent

Sources & evidence

ORD record
ord-4943d5f18cd84f95b4a9c9945a715b9a
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06022906

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes