Dichloromethane → (S)-3-Amino-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride hydrochloride

HRID 509907Notes

Reaction equation

HRID 509907 reaction equation
[Br-].C(OC([NH:9][C@H:10]1[CH2:15][CH2:14][CH2:13][N+:12]([CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])[CH:35]=2)([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:20]=2)[CH2:11]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[Cl:53]CCl>>[ClH:53].[Cl-:53].[NH2:9][C@H:10]1[CH2:15][CH2:14][CH2:13][N+:12]([CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([O:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])[CH:35]=2)([CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])[CH:20]=2)[CH2:11]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 117856394(S)-3-tert-Butoxycarbonylamino-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium bromide

Product 1

HCID 117856338(S)-3-Amino-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium chloride hydrochloride

Procedure

(S)-3-tert-Butoxycarbonylamino-1,1-bis-[3-(3-methoxycarbonylmethoxy-phenyl)-propyl]-piperidinium bromide (707 mg, 1.0 mmol) is dissolved in dichloromethane (1 ml) and trifluoroacetic acid (1 ml) and stirred at room temperature overnight. The mixture is evaporated, dissolved in acetonitrile and 1 M HCl (5 ml) and evaporated again. LC (method L): tR=0.99 min; Mass spectrum (ESI+): m/z=513 [M]+.

Workup

  1. customThe mixture is evaporated
  2. dissolutiondissolved in acetonitrile
  3. custom1 M HCl (5 ml) and evaporated again

Sources & evidence

ORD record
ord-0bc83e3a174e4e889a268e97f26c9902
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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