Hydrochloric Acid → HCID 20540393, compound

HRID 1065470Notes

Reaction equation

HRID 1065470 reaction equation
[C:1]([C:4]1[CH:36]=[CH:35][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([NH:19][CH2:20][CH2:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=O)[NH2:2].O.[ClH:38]>O1CCCC1.B#B>[ClH:38].[ClH:38].[NH2:2][CH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([NH:19][CH2:20][CH2:21][CH:22]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH3:18])=[CH:12][CH:11]=2)=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13065250HCID 13065250, compound

Product 1

HCID 20540393HCID 20540393, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 6328200DiboronSolvent

Procedure

To the suspension of 5.0 g of racemic 1-[4-(4-carbamoylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane (Example 10/7) in 75 ml of tetrahydrofuran, 70 ml of 1-molar diborane in tetrahydrofuran are added dropwise while stirring under nitrogen at 0°. It is refluxed for 18 hours, cooled to 0° again and 30 ml of water are added dropwise, followed by 15 ml of concentrated hydrochloric acid. The mixture is evaporated, warmed with 50 ml of methanol, evaporated again and the residue is recrystallized from ethanol, to yield the 1-(4-(4-aminomethylbenzyloxy)-phenyl]-2-(3,3-diphenylpropylamino)-propane dihydrochloride melting at 259°-262°.

Workup

  1. additionare added dropwise
  2. temperatureIt is refluxed for 18 hours
  3. temperaturecooled to 0° again
  4. customThe mixture is evaporated
  5. temperaturewarmed with 50 ml of methanol
  6. customevaporated again
  7. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-4af2ea87246343ac9c3890535bfc5f3e
Source dataset
uspto-grants-1982_05
Patent number
US04329367

Reaction notes

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