Sodium Carbonate → Tert-butyl (2-(tert-butoxycarbonylaminomethyl)anilino)piperidine carboxylate

HRID 2294927Notes

Reaction equation

HRID 2294927 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=1[NH:12][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][N:24]1[C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4409487tert-butyl N-[(2-aminophenyl)methyl]carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 54015391Tert-butyl (2-(tert-butoxycarbonylaminomethyl)anilino)piperidine carboxylateYield 106.4%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 15.5 g of 2-(tert-butoxycarbonylaminomethyl)aniline, 15 g of N-t-butyloxycarbonyl-4-piperidone, 250 mL of 1,2-dichloroethane, 4.2 mL of glacial acetic acid and 25 g of sodium triacetoxyborohydride was stirred at room temperature for 48 h. The reaction mixture was poured into 500 mL chloroform and 500 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 2×250 mL of chloroform and the combined organic layers dried over MgSO4 and concentrated under reduced pressure. Drying overnight under vacuum gave 30.1 g of tert-butyl (2-(tert-butoxycarbonylaminomethyl)anilino)piperidine carboxylate as a solid: 1H NMR (400 MHz, CDCl3) 7.19 (t, 1H), 7.0 (d, 1H), 6.6 (dd, 2H), 4.94 (br s, 1H), 4.75 (br s, 1H), 4.23 (br m, 2H), 4.0 (br m, 2H), 3.45 (br m, 1H), 3.0 (br m, 2H), 2.0 (br m, 2H), 1.82 (br m, 1H), 1.46 (s, 9H), 1.44 (s, 9H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×250 mL of chloroform
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customDrying overnight under vacuum

Sources & evidence

ORD record
ord-4aad9fe7b0b14412bd4f2c4209e19d89
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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