Hydrochloric Acid → HCID 20540361, compound

HRID 1065473Notes

Reaction equation

HRID 1065473 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:18][C:19](=O)[CH2:20][CH:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[ClH:37]>O1CCCC1.B>[ClH:37].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:18][CH2:19][CH2:20][CH:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH3:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 13065283HCID 13065283, compound

Product 1

HCID 20540361HCID 20540361, compound

Reagents, catalysts & solvents 2

HCID 6331BoraneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the suspension of 11.2 g of dl-1-(p-benzyloxyphenyl)-2-(3,3-diphenylpropionamido)-propane in 200 ml of tetrahydrofuran, 150 ml of 1 molar borane in tetrahydrofuran are added dropwise while stirring under nitrogen at 0°. The mixture is refluxed overnight, cooled to 0° and treated dropwise with 150 ml of methanol, followed by 30 ml of concentrated hydrochloric acid. The mixture is evaporated, again treated with 150 ml of methanol, warmed to 50° and evaporated. The resulting white solid is recrystallized from isopropanol containing a little methanol to afford the dl-1-(p-benzyloxyphenyl)-2-(3,3-diphenylpropylamino)-propane hydrochloride, melting at 187°-190°.

Workup

  1. additionare added dropwise
  2. temperatureThe mixture is refluxed overnight
  3. temperaturecooled to 0°
  4. customThe mixture is evaporated
  5. additionagain treated with 150 ml of methanol
  6. temperaturewarmed to 50°
  7. customevaporated
  8. customThe resulting white solid is recrystallized from isopropanol containing a little methanol

Sources & evidence

ORD record
ord-301047c923ae40f2a9706b1b4290532e
Source dataset
uspto-grants-1982_05
Patent number
US04329367

Reaction notes

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