Hydrochloric Acid → HCID 66593400, compound

HRID 1091656Notes

Reaction equation

HRID 1091656 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][N:12]2C(OC(C)(C)C)=O)=[O:10])=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25].[ClH:27]>O1CCOCC1>[ClH:27].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][NH:12]2)=[O:10])=[CH:4][C:3]=1[N+:24]([O-:26])=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66593418HCID 66593418, compound

Product 1

HCID 66593400HCID 66593400, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

(R)-tert-Butyl 2-[(4-amino-3-nitrophenyl)aminocarbonyl]piperidine-1-carboxylate (4.80 g, 13.2 mmol) was suspended in dioxane (100 mL) and hydrogen chloride (75 mL of a 4M solution in dioxane) was added. The resulting dark colored solution was stirred at room temperature for 3.5 hr resulting in a yellow/brown suspension. The solid was collected by filtration and briefly dried under high vacuum. The solid was suspended in water, the pH was adjusted to pH 8 with 1M sodium carbonate solution and the resulting suspension stirred for 15 minutes. The solid was collected and dried under high vacuum to give (R)—N-(4-amino-3-nitrophenyl)piperidine-2-carboxamide hydrochloride salt as an orange solid (2.08 g). This was treated with 1M sodium carbonate solution (200 mL) and extracted with EA (3×). The combined EA extracts were washed with brine, dried over magnesium sulfate, and concentrated to give (R)—N-(4-amino-3-nitrophenyl)piperidine-2-carboxamide as an orange foam (1.77 g).

Workup

  1. customresulting in a yellow/brown suspension
  2. filtrationThe solid was collected by filtration
  3. custombriefly dried under high vacuum
  4. stirringthe resulting suspension stirred for 15 minutes
  5. customThe solid was collected
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-806b88afa64e490ebdf7f25f0cc59f2b
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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