4-Bromoaniline → Tert-butyl 4-((4-bromophenyl)amino)piperidine-1-carboxylate

HRID 531458

Reaction equation

HRID 531458 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(=O)C.ClC(Cl)C>[Br:15][C:16]1[CH:22]=[CH:21][C:19]([NH:20][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 78074-BromoanilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 11210451Tert-butyl 4-((4-bromophenyl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-133, tert-butyl 4-oxopiperidine-1-carboxylate (3 gm, 15.0 mmol) and 4-bromoaniline (2.59 gm, 15.0 mmol) were reacted using Na(OAc)3BH (105 mg, 0.494 mmol) and 3 drops of acetic acid in dichloroethane (80 mL) to afford 6.7 gm (crude) of the titled compound. MS: m/z=256.8 (M-Boc+1).

Workup

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Sources & evidence

ORD record
ord-7b05fc1244c24a98b9729c665c793f84
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Linked notes

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