HCID 131712693, compound → HCID 131712692, compound

HRID 2198949Notes

Reaction equation

HRID 2198949 reaction equation
[ClH:1].[CH3:2][N:3]([CH3:24])[CH2:4][CH2:5][CH2:6][C:7]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([OH:17])[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1O>Cl>[ClH:1].[CH3:2][N:3]([CH3:24])[CH2:4][CH2:5][CH2:6][C:7]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:17]1

Participants

3

Reactant 1

HCID 131712693HCID 131712693, compound

Product 1

HCID 131712692HCID 131712692, compoundYield 10,634.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A sample of crude α-[3-(dimethylamino)propyl]-2-hydroxy-α-phenylbenzenepropanol, hydrochloride (1:1) (2 g, 0.017 mmoles) is heated in 100 ml of dilute HCl at 100° C. for 2 hours, cooled and extracted with ether. The aqueous is basified with 10% sodium hydroxide and extracted 4 times with chloroform. The organics are dried (carbonate) and evaporated to 1.8 g of oil which partially crystallized on standing. This is taken up in ether and converted to the hydrochloride which oiled out. Trituration with ethyl acetate gives 0.6 g of white solid (32%). This is recrystallized by dissolving in dichloromethane, adding 30 ml of ethyl acetate, and boiling down to 20 ml. Standing at 25° C. gives, after drying at 80° C., 0.4 g, 3,4-dihydro-N,N-dimethyl-2-phenyl-2H-1-benzopyran-2-propanamine, hydrochloride (1:1) mp 126°-128° C.

Workup

  1. temperaturecooled
  2. extractionextracted with ether
  3. extractionextracted 4 times with chloroform
  4. dry with materialThe organics are dried (carbonate)
  5. customevaporated to 1.8 g of oil which
  6. custompartially crystallized

Sources & evidence

ORD record
ord-870e2615091a47f1b95008b3a9f1e204
Source dataset
uspto-grants-1982_11
Patent number
US04360532

Reaction notes

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