Hydrochloric Acid → 2-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine hydrochloride

HRID 710235Notes

Reaction equation

HRID 710235 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[O:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)=[CH:12][CH:11]=1.[ClH:29]>O1CCOCC1>[ClH:29].[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131733926tert-Butyl 2-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine-4-carboxylate

Product 1

HCID 896907602-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 2-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine-4-carboxylate (330 mg, 0.87 mmol) was dissolved in dioxane (12 ml) and a solution of HCl in dioxane (4M, 3.25 ml, 13 mmol) was added. The reaction mixture was stirred overnight at room temperature. The solid was filtered off, washed with ether and dried in vacuo at 60° C. to afford 2-(4-(1H-benzo[d]imidazol-2-yl)phenyl)morpholine hydrochloride (232 mg, 85%) as an off-white solid. MS (ISP): 280.1 ([M+H]+).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with ether
  3. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-672975d8c27b48ba9664f9b2249016a4
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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