Hydrochloric Acid → Tert-butyl (1-(2-(1,2-dihydroxyethyl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 339672Notes

Reaction equation

HRID 339672 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[C:22]([CH:25]2[CH2:29][O:28]C(C)(C)[O:26]2)[CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.CCOC(C)=O.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[C:22]([CH:25]([OH:26])[CH2:29][OH:28])[CH:21]=[CH:20]3)[CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86654343Tert-butyl (1-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 86654344Tert-butyl (1-(2-(1,2-dihydroxyethyl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To tert-butyl(1-(2-(2,2-dimethyl-1,3-dioxolan-4-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (81 mg, 0.18 mmol) in THF (3 mL) was added HCl (20 mg, 0.55 mmol) (6M). The reaction was stirred for 3 hours at ambient temperature and then diluted with EtOAc (10 mL) and saturated NaHCO3 (5 mL). The phases were separated, and the organic layer was dried and concentrated to give crude product.

Workup

  1. customThe phases were separated
  2. customthe organic layer was dried
  3. concentrationconcentrated
  4. customto give crude product

Sources & evidence

ORD record
ord-7e6a234823d748cb8e0377c59d8a1187
Source dataset
uspto-grants-2014_11
Patent number
US08895550B2

Reaction notes

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