Water → HCID 15480566, compound

HRID 427261Notes

Reaction equation

HRID 427261 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16]1.O.CN(C)[CH:31]=[O:32]>>[C:22]1([CH2:21][N:18]2[CH2:19][CH2:20][CH:15]([N:14]3[C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=4[C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[NH:1][C:31]3=[O:32])[CH2:16][CH2:17]2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6228DimethylformamideHCID 15480565HCID 15480565, compound

Product 1

HCID 15480566HCID 15480566, compound

Conditions

Temperature
100 °C

Procedure

To a solution of 36.0 g (0.101 mol) of 2-amino-2′-[[1-(phenylmethyl)-4-piperidinyl]amino]-biphenyl in 200 mL of dimethylformamide were added 40.5 g (0.250 mol) of N,N′-carbonyldiimidazole, then the mixture was stirred for 2 hours at 100° C., after which the solvent was eliminated in vacuo. The residue was stirred with water, then extracted exhaustively with dichloromethane. The combined organic extracts were dried over sodium sulfate, clarified with active charcoal and evaporated down. The residue (60 g) was purified by chromatography on aluminium oxide of activity stage 3 using PE/EE 2/1 (v/v). The desired compound was obtained from the corresponding fractions in a yield of 6.2 g (16% of theory).

Workup

  1. extractionextracted exhaustively with dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. customevaporated down
  4. customThe residue (60 g) was purified by chromatography on aluminium oxide of activity stage 3 using PE/EE 2/1 (v/v)

Sources & evidence

ORD record
ord-0a14590731004311b9887781dbba447e
Source dataset
uspto-grants-2001_11
Patent number
US06313097B1

Reaction notes

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