Sodium hydride → HCID 20379203, compound

HRID 2051604Notes

Reaction equation

HRID 2051604 reaction equation
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]2[CH:15]=[CH:16][CH:17]=[CH:18][C:6]=2[CH:5]=1.[H-].[Na+].[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27]Cl>COC>[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:4]([O:3][C:2]([F:1])([F:19])[F:20])=[CH:5][C:6]2[CH:18]=[CH:17][CH:16]=[CH:15][C:7]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 20379200HCID 20379200, compound

Product 1

HCID 20379203HCID 20379203, compound

Reagents, catalysts & solvents 1

HCID 8254Dimethyl EtherSolvent

Procedure

10-Trifluoromethoxy-5H-dibenz[b,f]azepine (650 mg) was refluxed with NaH (600 mg, 57% suspension) in a solution of 3-dimethylaminopropyl chloride (ca. 2.0 g) in dimethyl ether (70 ml) overnight. The excess of NaH was destroyed with MeOH (10 ml) and the solvent removed under vacuum. The remaining gum was dissolved in ether (50 ml), washed with water (2×20 ml) and extracted into 2 N H2SO4 (2×20 ml). The extracts were combined, neutralized with NaHCO3 and extracted with ether (3×20 mls). The ether extracts were washed with water (2×20 mls), dried (Na2SO4) and the ether removed under vacuum.

Workup

  1. customThe excess of NaH was destroyed with MeOH (10 ml)
  2. customthe solvent removed under vacuum
  3. dissolutionThe remaining gum was dissolved in ether (50 ml)
  4. washwashed with water (2×20 ml)
  5. extractionextracted into 2 N H2SO4 (2×20 ml)
  6. extractionextracted with ether (3×20 mls)
  7. washThe ether extracts were washed with water (2×20 mls)
  8. dry with materialdried (Na2SO4)
  9. customthe ether removed under vacuum

Sources & evidence

ORD record
ord-c24da11df4654efcb991e3de033c5bb6
Source dataset
uspto-grants-1980_01
Patent number
US04181655

Reaction notes

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