Ammonia → HCID 86745326, compound

HRID 1461592Notes

Reaction equation

N.[H][H].[C:4]([CH2:6][CH2:7][O:8][CH:9]([O:11][CH2:12][CH2:13][C:14]#[N:15])[CH3:10])#[N:5].C[C:17](S[As](C)C)([C@@H:19]([NH2:23])C(O)=O)[CH3:18].NCCCOC(OCCCN)C.NCCCOC(O)C.NCCCOCCOCC[CH2:58][NH:59][CH2:60]CCOCCOCCCN>[Co].C(O)(C)(C)C>[NH2:15][CH2:14][CH2:13][CH2:12][O:11][CH:9]([O:8][CH2:7][CH2:6][CH2:4][NH2:5])[CH3:10].[CH3:58][N:59]([CH2:18][CH2:17][CH2:19][NH2:23])[CH3:60]

Participants

Conditions

Temperature: 90 °C

Procedure

Into a 300 ml autoclave was placed 10 g of Raney cobalt and 15 g of anhydrous ammonia. A heel of 30 ml of t-butanol was then pumped into the reactor and the reactor heated externally to 90° C. The pressure was then raised to 850 psig with hydrogen. The crude product mixture containing bis(2-cyanoethoxy)ethane and DMAPN from Example 1 was then pumped into the autoclave at a rate of 0.6 g/min until 150 g of the mixture had been admitted. During the addition, the temperature was maintained at 90° C. and the pressure at 850 psig. Following the addition, the reactor was stirred an additional 1 hr until hydrogen uptake was complete. Analysis of the product mixture by GC (t-butanol free basis) revealed the composition to be 21.5 wt % DMAPA. 73.5 wt % of bis(3-aminopropoxy)ethane, 0.72 wt % of 3-aminopropoxyethanol, 1.2 wt % of N-(dimethylamino)-bis(3-aminopropoxy)ethane and 3.1 wt % of bis(aminopropoxyethoxypropyl)amine.

Workup

additionDuring the addition
temperaturethe temperature was maintained at 90° C.
additionthe addition

Sources & evidence

ORD record: ord-e7144f18903947b793754b666c77287e
Source dataset: uspto-grants-1991_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05075507

Reaction notes

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