Heptanenitrile, 7-amino- → N~1~-Propylheptane-1,7-diamine

HRID 436663Notes

Reaction equation

HRID 436663 reaction equation
[C:1]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[N:13])(=O)[CH2:2][CH3:3].NCCCCCCC#N.C(Cl)(=O)CC.C(C(N)CCCCCCN)CC.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C1C=CC=CC=1.N1C=CC=CC=1>[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])[CH2:2][CH3:3]

Participants

9

Reactant 5

HCID 31676Heptanenitrile, 7-amino-HCID 62324Propionyl chlorideHCID 19028721HCID 19028721, compoundHCID 21226445Aluminium lithium hydrideHCID 21452875N-(6-Cyanohexyl)propanamide2×

Product 1

HCID 21452856N~1~-Propylheptane-1,7-diamine

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The intermediate N-n-propyl-1,7-heptanediamine was prepared in two steps following the procedure described in Example 119. There was first obtained, as an amber liquid, 14.4 g. of 7-propionamidoheptanonitrile using 10.0 g. of 7-aminoheptanonitrile, 8.1 g. of propionyl chloride, 6.9 g. of pyridine and 100 ml. of benzene. Next was obtained 9.3 g. of n-propyl-1,7-heptanediamine, b.p. 112°-116° C. at 5 mm., using 8.0 g. of lithium aluminum hydride in 900 ml. of tetrahydrofuran and 18.2 g. of 7-propionamidoheptanonitrile in 100 ml. of tetrahydrofuran.

Workup

  1. customThere was first obtained, as an amber liquid, 14.4 g
  2. customNext was obtained 9.3 g

Sources & evidence

ORD record
ord-a337065dd3cf46e3aebf5d7dfcbbd398
Source dataset
uspto-grants-1977_02
Patent number
US04009208

Reaction notes

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