3-Chloro-1-propanol → PF-244

HRID 1581123Notes

Reaction equation

HRID 1581123 reaction equation
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][CH:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:32][CH2:33][CH2:34][CH2:35][OH:36]>>[ClH:32].[C:26]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:33][CH2:34][CH2:35][OH:36])[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 123133-Chloro-1-propanolHCID 12831215HCID 12831215, compound

Product 1

HCID 161793PF-244

Procedure

To bis(3,3-diphenylpropyl)amine (1.2 g) was added 3-chloropropan-1-ol (20 ml) and the mixture was heated with agitation at 150° to 160°C for 4 hours. The reaction mixture was evaporated under reduced pressure, and to the resulting residue was added benzene (20 ml). The mixture was washed with 5% hydrochloric acid and water in order. The benzene layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give oily residue. The residue thus obtained was crystallized from acetone-petroleum ether and further recrystallized from ethanol-ether to give 3-[bis(3,3-diphenylpropyl)amino]propan-1-ol hydrochloride (0.5 g). M.P. 152° to 154°C.

Workup

  1. temperaturethe mixture was heated with agitation at 150° to 160°C for 4 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. additionto the resulting residue was added benzene (20 ml)
  4. washThe mixture was washed with 5% hydrochloric acid and water in order
  5. dry with materialThe benzene layer was dried over anhydrous sodium sulfate
  6. customevaporated under reduced pressure
  7. customto give oily residue
  8. customThe residue thus obtained
  9. customwas crystallized from acetone-petroleum ether
  10. customfurther recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-c1f99356e4d4426185fd4660aed75f20
Source dataset
uspto-grants-1976_01
Patent number
US03935268

Reaction notes

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