Ammonia → HCID 129953, compound

HRID 247466Notes

Reaction equation

HRID 247466 reaction equation
Cl.C[O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([NH:14][CH2:15][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[OH:17])[CH2:11]2)=[CH:6][CH:5]=1.B(Br)(Br)Br.N>C(Cl)Cl>[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([NH:14][CH2:15][CH:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[OH:17])[CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 25134Boron tribromideHCID 19888695HCID 19888695, compound

Product 1

HCID 129953HCID 129953, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a suspension of 3.7 g of 2-[(7-methoxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-(3-chlorophenyl) ethanol hydrochloride, obtained as described in Example 7, in 60 ml of anhydrous methylene chloride, there is added dropwise, under a nitrogen stream and at the temperature of -20° C., 60 ml of a 1M solution of boron tribromide in methylene chloride. The reaction mixture is left under stirring at the temperature of -20° C. for 3 hours and 30 minutes. An excess of ice is added and the mixture is made alkaline with concentrated ammonia. The organic phase is separated, dried over anhydrous sodium sulfate and evaporated to dryness. The residue thus obtained is purified by flash-chromatography using a mixture of methylene chloride/methanol 9/1 for the elution. The 2-[(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-(3-chlorophenyl)ethanol, thus obtained in the form of basis, is dissolved in a mixture of 10 ml of isopropyl alcohol and 30 ml of ethyl ether. To the resulting solution there is added a saturated solution of hydrogen chloride in isopropyl alcohol to obtain the 2-[(7-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)amino]-1-(3-chlorophenyl)-ethanol hydrochloride, designated by its code number SR 58339 A, which, after crystallization from 20 ml of absolute ethanol, melts at 113°-115° C. Yield: 30% of the theoretical value.

Workup

  1. customobtained
  2. additionthere is added dropwise, under a nitrogen stream
  3. waitThe reaction mixture is left
  4. additionAn excess of ice is added
  5. customThe organic phase is separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe residue thus obtained
  9. customis purified by flash-chromatography
  10. additiona mixture of methylene chloride/methanol 9/1
  11. washfor the elution

Sources & evidence

ORD record
ord-4e8b530024c84e8c97007cdf314bc802
Source dataset
uspto-grants-1987_11
Patent number
US04707497

Reaction notes

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