Sodium borohydride → HCID 70532723, compound

HRID 1902673Notes

Reaction equation

HRID 1902673 reaction equation
[BH4-].[Na+].[I-].[CH3:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[O:8][C:9]1[CH:14]=[CH:13][N+:12]([CH2:15][CH2:16][CH2:17][N:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:11][CH:10]=1.[C:34]([OH:41])(=[O:40])[CH:35]=[CH:36][C:37]([OH:39])=[O:38].CC1C=C(C=CC=1)OC1CCN(CCCN(C2C=CC=CC=2)C2C=CC=CC=2)CC1>CO>[C:34]([OH:41])(=[O:40])[CH:35]=[CH:36][C:37]([OH:39])=[O:38].[CH3:4][C:5]1[CH:6]=[C:7]([CH:31]=[CH:32][CH:33]=1)[O:8][C:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:11][CH:10]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 20482609HCID 20482609, compoundHCID 70531914HCID 70531914, compound

Product 1

HCID 70532723HCID 70532723, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.0 g. of sodium borohydride, (0.131 moles) is added portionwise to a solution of 13 g. (0.032 moles) of 4-(3-methylphenoxy)-1-[3-(N,N-diphenylamino)propyl]pyridinium iodide in 200 ml. of methanol over a 10 minute period, allowing the temperature to reach reflux. The reaction is refluxed another 20 minutes. Solvent is evaporated. The residue is dissolved in chloroform, washed with sodium carbonate solution, and dried. Solvent is evaporated. The residue is converted to the maleate in ether and recrystallized from acetonitrile to give 10.9 g. of 3,5-dihydro-4-(3-methylphenoxy)-N,N-diphenyl-1(2H)-pyridinepropanamine butenedioate (1:1), mp. 164°-166° C.

Workup

  1. temperatureto reach reflux
  2. temperatureThe reaction is refluxed another 20 minutes
  3. customSolvent is evaporated
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed with sodium carbonate solution
  6. customdried
  7. customSolvent is evaporated
  8. customrecrystallized from acetonitrile
  9. customto give 10.9 g

Sources & evidence

ORD record
ord-a0416846cb8e4bb5aea5ad3d530edc69
Source dataset
uspto-grants-1982_12
Patent number
US04364954

Reaction notes

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